Granted Patent
B2
US 12,428,662 · App. 17/355,912 · Granted Sep 30, 2025
Methods for making high intensity sweeteners
Inventors:
Andrew P. Patron (San Marcos, CA); Chris Edano Noriega (San Diego, CA); Rama R. Manam (San Diego, CA); Justin Colquitt (San Diego, CA); Nathan Faber (San Diego, CA); Helge Zieler (Del Mar, CA); Justin Stege (San Diego, CA)
Assignee:
FIRMENICH INCORPORATED
C12P33/00A23L27/36C07J17/005C12N9/0042C12N9/244C12N9/90C12P33/12C12P33/20C12Y106/02004C12Y302/01006C12Y504/99003A23V2002/00C12P19/18C12P19/56
View Patent ↗
Loading inventors, assignments & file history…
Abstract
Provided herein include methods of making mogroside compounds, e.g., Compound 1, compositions (for example host cells) for making the mogroside compounds, and the mogroside compounds made by the methods disclosed herein, and compositions (for example, cell lysates) and recombinant cells comprising the mogroside compounds (e.g., Compound 1). Also provided herein are novel cucurbitadienol synthases and the use thereof.
Claims (11)
1. A method of producing Compound 1 having the structure of:
the method comprising:
contacting mogroside III E with an enzyme capable of catalyzing a production of Compound 1 from mogroside III E ;
wherein the enzyme is selected from the group consisting of: β-glucosidases, transglucosidases,
a cyclomaltodextrin glucanotransferase (CGTase) comprising an amino acid sequence having at least 90% sequence identity to any one of SEQ ID NOs: 3, 78-82, 85-87, 89-92, 94, 95, 98, 101, and 154, and
a dextransucrase comprising an amino acid sequence having at least 90% sequence identity to any one of SEQ ID NOs: 106-109, 156, and 896.
2. The method of claim 1 , wherein contacting mogroside III E with the enzyme comprises contacting mogroside III E with a recombinant host cell that comprises a gene encoding the enzyme.
3. The method of claim 2 , wherein the gene is heterologous to the recombinant host cell.
4. The method of claim 2 , wherein the mogroside III E is present in and/or produced by the recombinant host cell.
5. The method of claim 2 , comprising cultivating the recombinant host cell in a culture medium under conditions in which the enzyme is expressed.
6. The method of claim 1 , wherein the enzyme is a CGTase comprising an amino acid of any one of SEQ ID NOs: 3, 78-82, 85-87, 89-92, 95, 98, 101, 148, and 154.
Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Jun 24, 2021
From: PATRON, ANDREW P.; NORIEGA, CHRIS EDANO; MANAM, RAMA R.; COLQUITT, JUSTIN; FABER, NATHAN; ZIELER, HELGE; STEGE, JUSTIN
To: SENOMYX, INC.
Reel/Frame 056657/0120 →
MERGER AND CHANGE OF NAME
Recorded Jun 24, 2021
From: SENOMYX, INC.; FIRMENICH INCORPORATED
To: FIRMENICH INCORPORATED
Reel/Frame 056657/0167 →
Continuity (4)
Provisional Application
62551750
· Aug 29, 2017
Provisional Application
62501018
· May 3, 2017
References Cited (248)
US 6468576B1
· Sher et al.
· 2002
[cited by applicant]
US 7659097B2
· Renninger et al.
· 2010
[cited by applicant]
US 8236512B1
· Zhao et al.
· 2012
[cited by applicant]
US 8357527B2
· Ubersax
· 2013
[cited by applicant]
US 8367395B2
· Bailey et al.
· 2013
[cited by applicant]
US 8415136B1
· Gardner et al.
· 2013
[cited by applicant]
US 8470568B2
· Walker et al.
· 2013
[cited by applicant]
US 8481286B2
· Julien et al.
· 2013
[cited by applicant]
US 8519204B2
· Ohler et al.
· 2013
[cited by applicant]
US 8586814B2
· Fisher et al.
· 2013
[cited by applicant]
US 8603800B2
· Gardner et al.
· 2013
[cited by applicant]
US 8609371B2
· Julien et al.
· 2013
[cited by applicant]
US 8753842B2
· Julien et al.
· 2014
[cited by applicant]
US 8859261B2
· Gardner et al.
· 2014
[cited by applicant]
US 9200296B2
· Renninger et al.
· 2015
[cited by applicant]
US 9410214B2
· Hawkins et al.
· 2016
[cited by applicant]
US 9540662B2
· Walker et al.
· 2017
[cited by applicant]
US 20110027413A1
· Jia
· 2011
[cited by applicant]
US 20140170286A1
· Jia
· 2014
[cited by applicant]
US 20170105432A1
· Karanewsky et al.
· 2017
[cited by applicant]
US 20170283844A1
· Itkin et al.
· 2017
[cited by applicant]
US 20170354175A1
· Karanewsky et al.
· 2017
[cited by applicant]
US 20180014565A1
· Ahmet et al.
· 2018
[cited by applicant]
US 20180020707A1
· Ahmet et al.
· 2018
[cited by applicant]
US 20180020709A1
· Markosyan
· 2018
[cited by applicant]
US 20180086751A1
· Karanewsky et al.
· 2018
[cited by applicant]
US 20240065302A1
· Manam
· 2024
[cited by applicant]
US 20240090547A1
· Manam
· 2024
[cited by applicant]
US 20240108040A1
· Patron et al.
· 2024
[cited by applicant]
US 20240188613A1
· Manam
· 2024
[cited by applicant]
US 20240240222A1
· Noriega
· 2024
[cited by applicant]
CN 105039274
· 2015
[cited by applicant]
EP 2783009B1
· 2016
[cited by applicant]
WO WO9957250
· 1999
[cited by applicant]
WO WO05015158
· 2005
[cited by applicant]
WO WO05041684
· 2005
[cited by applicant]
WO WO06084186
· 2006
[cited by applicant]
WO WO06138512
· 2006
[cited by applicant]
WO WO07124152
· 2007
[cited by applicant]
WO WO08154221
· 2008
[cited by applicant]
WO WO09023975
· 2009
[cited by applicant]
WO WO09100333
· 2009
[cited by applicant]
WO WO09111447
· 2009
[cited by applicant]
WO WO10014666
· 2010
[cited by applicant]
WO WO10014813
· 2010
[cited by applicant]
WO WO11112892
· 2011
[cited by applicant]
WO WO11123693
· 2011
[cited by applicant]
WO WO12021837
· 2012
[cited by applicant]
WO WO12061698
· 2012
[cited by applicant]
WO WO12103074
· 2012
[cited by applicant]
WO WO13025560
· 2013
[cited by applicant]
WO WO13076577
· 2013
[cited by applicant]
WO WO13096420
· 2013
[cited by applicant]
WO WO14025706
· 2014
[cited by applicant]
WO WO14027118
· 2014
[cited by applicant]
WO WO14086842
· 2014
[cited by applicant]
WO WO14130513
· 2014
[cited by applicant]
WO WO14140634
· 2014
[cited by applicant]
WO WO14146089
· 2014
[cited by applicant]
WO WO14130582
· 2014
[cited by applicant]
WO WO14086842A9
· 2015
[cited by applicant]
WO WO15082012
· 2015
[cited by applicant]
WO WO15168779
· 2015
[cited by applicant]
WO WO16038617
· 2016
[cited by applicant]
WO WO16050890
· 2016
[cited by applicant]
WO WO16060276
· 2016
[cited by applicant]
WO WO16073251
· 2016
[cited by applicant]
WO WO16130609
· 2016
[cited by applicant]
WO WO17044659
· 2017
[cited by applicant]
WO WO17172766
· 2017
[cited by applicant]
WO WO17176873
· 2017
[cited by applicant]
WO WO18016483
· 2018
[cited by applicant]
WO WO18200663
· 2018
[cited by applicant]
WO WO18229283
· 2018
[cited by applicant]
WO WO19169027
· 2019
[cited by applicant]
WO WO19202402
· 2019
[cited by applicant]
WO WO20033420
· 2020
[cited by applicant]
WO WO20096905
· 2020
[cited by applicant]
WO WO20097588
· 2020
[cited by applicant]
WO WO20112957
· 2020
[cited by applicant]
WO WO20201446
· 2020
[cited by applicant]
WO WO20205978
· 2020
[cited by applicant]
WO WO21216504
· 2021
[cited by applicant]
US 8,486,659 B2, 07/2013, Julien et al. (withdrawn)
[cited by applicant]
Deng et al., 2018, Efficient expression of cyclodextrin glycosyltransferase from Geobacillus stearothermophilus in
[cited by applicant]
Ji et al., May 15, 2013, Recent progress in biochemical properties and functions of UDP-glycosyltransferase during plant secondary metabolism, Food Science, 34(9):316-323.
[cited by applicant]
Lee et al., 2017, Optimization of leucrose production by dextransucrase from
[cited by applicant]
Monchois et al., 1996, Cloning and sequencing of a gene coding for a novel dextransucrase from Leuconostoc mesenteroides NRRL B-1299 synthesizing only a(1-6) and a(1-3) linkages, Gene, 182:23-32.
[cited by applicant]
Ager et al., 1998, Commercial, synthetic nonnutritive sweeteners, Angew. Chem. Int. Ed. 37:1802-1817.
[cited by applicant]
Akihisa et al., 2007, Cucurbitane glycosides from the fruits of siraitia grosvenorii and their inhibitory effects on Epstein-Barr virus activation, J. Nat. Prod., 70:783-788.
[cited by applicant]
Altschul et al., 1996, [27] Local Alignment Statistics, Methods in Enzymology, 266:460-480.
[cited by applicant]
Altschul et al., 1997, Gapped BLAST and PSI-BLAST: a new generation of protein database search programs, Nucleic Acids Res., 25(17):3389-3402.
[cited by applicant]
Andrade-Eiroa et al., Jun. 2016, Solid-phase extraction of organic compounds: A critical review (Part I), TrAC Trends in Analytical Chemistry, 80:641-654.
[cited by applicant]
Cardenas et al., 2016, Engineering cofactor and transport mechanisms in
[cited by applicant]
Chabrol, 2012, The hideous price of beauty an investigation into the market of deep-sea shark liver oil. Edited by: The Bloom Association.
[cited by applicant]
Chang et al., 2007, Engineering Escherichia coli for production of functionalized terpenoids using plant P450s. Nat Chem Biol, 3:274-277.
[cited by applicant]
Chaturvedula et al., 2011, Enzymatic and acid hydrolysis of steviol and cucurbitane glycosides, Int. J. Pharm. Biomed. Res., 2(2):135-139.
[cited by applicant]
Chaturvedula et al., Jan. 2011, Comparative phytochemical studies of the commercial extracts of Siraitia grosvenorii, Journal of Pharmacy Research, 4(9):3166-3167.
[cited by applicant]
Chen et al., 2018, Kumada arylation of secondary amides enabled by chromium catalysis for unsymmetric ketone synthesis under mild conditions, ACS Catalysis, 8:5864-5868.
[cited by applicant]
Chen et al., Jan. 2005, Cucurbitacins and cucurbitane glycosies: structures and biologial activities, Natural Product Reports, 22(3), 14 pp.
[cited by applicant]
Chiu et al., 2013, Biotransformation of mogrosides from siraitia grosvenoril swingle by
[cited by applicant]
Dai et al., 2015, Functional characterization of cucurbtadienol synthase and triperpene glycosyltransferase involved in biosynthesis of mogrosides from siraitia grosvenoril, Plant Cell Physiol., 56(6):1172-1182.
[cited by applicant]
De Felipe et al., 2004, Targeting of Proteins Derived from Self-Processing Polyproteins Containing Multiple Signal Sequences, Traffic, 5:616-626.
[cited by applicant]
De Felipe, 2004, Skipping the co-expression problem: the new 2A “CHYSEL” technology, Genetic Vaccines and Ther. 2:13.
[cited by applicant]
Devos et al., 2000, Practical limits of function prediction, Proteins: Structure, Function, and Genetics, 41:98-107.
[cited by applicant]
Donald et al., Sep. 1997, Effects of Overproduction of the Catalytic Domain of 3-Hydroxy-3-Methylglutaryl Coenzyme A Reductase on Squalene Synthesis in
[cited by applicant]
GenBank: AEM42982.1, cucurbitadienol synthase [Siraitia grosvenorii], Dec. 1, 2012, 2 pp.
[cited by applicant]
Ghimire et al., 2009, Improved squalene production via modulation of the methylerythritol 4-phosphate pathway and heterologous expression of genes from Streptomyces peucetius ATCC 27952 in
[cited by applicant]
Ghimire et al., 2016, Advances in Biochemistry and Microbial Production of Squalene and Its Derivatives. J Microbiol Biotechnol, 26:441-451.
[cited by applicant]
Gruchattka et al., Dec. 23, 2015, In Vivo Validation of in Silico Predicted Metabolic Engineering Strategies in Yeast: Disruption of α-Ketoglutarate Dehydrogenase and Expression of ATP-Citrate Lyase for Terpenoid Produc…
[cited by applicant]
Itkin et al., 2016 The biosynthetic pathway of the nonsugar, high-intensity sweetener mogroside V from siraitia grosvenorii, PNAS, 113(47):E7619-E7628 and supplemental material.
[cited by applicant]
Jia et al., 2009, A minor, sweet cucurbitane glycoside from siraitia grosvenoril, Natural Product Communications, 4(6):769-772.
[cited by applicant]
Joska et al., May 2014 A universal cloning method based on yeast homologous recombination that is simple, efficient, and versatile, J. Microbiol. Methods, 100: 46-51.
[cited by applicant]
Kasal et al., 1988, Glycosides from Chinese medicinal plant, hemsleya panacis-scandens, and structure-taste relationship of cucurbitane glycosides, Chemical and Pharmaceutical Bulletin, 36(1):234-243.
[cited by applicant]
Katabami et al., 2015, Production of squalene by squalene synthases and their truncated mutants in
[cited by applicant]
Kinghorn et al., 1998, Noncariogenic intense natural sweeteners, Med. Res. Rev. 18(5):347-360.
[cited by applicant]
Kirby et al. Engineering triterpene production in
[cited by applicant]
Kisselev, Jan. 2002, Polypeptide release factors in prokaryotes and eukaryotes: same function, different structure, Structure, 10:8-9.
[cited by applicant]
Kozak et al., 2014, Engineering acetyl coenzyme A supply: functional expression of a bacterial pyruvate dehydrogenase complex in the cytosol of
[cited by applicant]
Lemaigre and Rousseau, Transcriptional control of genes that regulate glycolysis and gluconeogenesis in adult liver, Biochem. J. 303:1-14 (1994).
[cited by applicant]
LeVan et al., 2008, Section 16: Adsorbents and Ion Exchange, In Perry's Chemical Engineers' Handbook, 8th edition. Green ed., McGraw-Hill, New York, pp. 16-1-16-10.
[cited by applicant]
Lewin, Genes V (Oxford University Press, Oxford), pp. 847-873.
[cited by applicant]
Li et al., 2006, Cucurbitane glycosides from unripe fruits of Lo Han Kuo (siraitia grosvenori), Chem. Pharm. Bull, 54(10):1425-1428.
[cited by applicant]
Li et al., 2007, Cucurbitane glycosides from unripe fruits of siraitia grosvenori, Chem. Pharm. Bull. 55(7):1082-1086.
[cited by applicant]
Li et al., 2014, Chemistry and pharmacology of siraitia grosvenoril: a review, Chinese Journal of Natural Medicines, 12(2):89-102.
[cited by applicant]
Li et al., 2017, Cucurbitane glycosides from the fruit of siraitia grosvenori and their effects on glucose uptake in human HepG2 cells in vitro, Food Chemistry, 228:567-573.
[cited by applicant]
Loeken et al., 1993, Effects of mutation of the CREB binding site of the somatostatin promoter on cyclic AMP responsiveness in CV-1 cells, Gene Expr. 3:253-264.
[cited by applicant]
Luo et al., 2016, Liquid chromatography with tandem mass spectrometry method for the simultaneous determination of multiple sweet mogrosides in the fruits of siraitia grosvenoril and its marketed sweeteners, J. Sep. Sci…
[cited by applicant]
Matsumoto et al., 1990, Minor cucurbitane-glycosides from fruits of siraitia grosvenori (cucurbitaceae), Chem. Pharm. Bull., 38(7):2030-2032.
[cited by applicant]
McGehee et al., 1993, Differentiation-specific element: a cis-acting developmental switch required for the sustained transcriptional expression of the angiotensinogen gene during hormonal-induced differentiation of 3T3-…
[cited by applicant]
Mehrotra et al., 2014, Steviol glycosides and their use in food processing: a review, Innovare Journal of Food Science, 2(1):7-13.
[cited by applicant]
Narendranath et al., May 2005, Relationship between pH and Medium Dissolved Solids in Terms of Growth and Metabolism of Lactobacilli and
[cited by applicant]
Newman et al., 2006, High-level production of amorpha-4, 11-diene in a two-phase partitioning bioreactor of metabolically engineered
[cited by applicant]
Noguchi et al., May 2008, Sequential glucosylation of a furofuran lignan, (+)-sesaminol, by Sesamum indicum UGT71A9 and UGT94D1 glucosyltransferases, Plant J., 54(3):415-427.
[cited by applicant]
O'Reilly et al., 1992, Identification of an Activating Transcription Factor( ATF) Binding Site in the Human Transforming Growth Factor-/32 Promoter, J. Biol. Chem. 267:19938-19943.
[cited by applicant]
Pandey et al., 2014, Enzymatic Biosynthesis of Novel Resveratrol Glucoside and Glycoside Derivatives, Applied and Environmental Microbiology, 80(23):7235-7243.
[cited by applicant]
Peng et al., 2015, Controlling heterologous gene expression in yeast cell factories on different carbon substrates and across the diauxic shift: a comparison of yeast promoter activities, Microb Cell Fact, 14:91.
[cited by applicant]
Płotka-Wasylka J et al., New Polymeric Materials for Solid Phase Extraction, Crit Rev Anal Chem., published online on Apr. 11, 2017, pp. 373-383.
[cited by applicant]
Prakash et al., 2014, Additional new minor cucurbitane clycosieds from Siraitia grosvenorii, Molecules, 19:3669-3680.
[cited by applicant]
Prakash et al., Jul. 2008, development of reblana, a natural, non-caloric sweetener, Food and Chemical Toxicology, 9 pp.
[cited by applicant]
Qing et al., 2017, Systematic identification of flavonols, flavonol glycosides, triterpene and siraitic acid glycosides from siraitia grosvenoril using high-performance liquid chromatography/quadrupole-time-of-flight ma…
[cited by applicant]
Rodriguez et al., 2016, ATP citrate lyase mediated cytosolic acetyl-CoA biosynthesis increases mevalonate production in
[cited by applicant]
Sajid et al., May 2017, Porous membrane protected micro-solid-phase extraction: A review of features, advancements and applications, Anal Chim Acta., 965:36-53.
[cited by applicant]
Salmon et al., Jul. 2016, A conserved amino acid residue critical for product and substrate specificity in plant triterpene synthases, Proc Natl Acad Sci U S A. 26; 113(30): E4407-E4414.
[cited by applicant]
Sawai et al. Triterpenoid Biosynthesis and Engineering in Plants, Front Plant Sci. Jun. 30, 2011; 2:25.
[cited by applicant]
Shen et al., 2014, Rapid Identification and quantification of five major mogrosides in siraitia grosvenoril (Luo-Han-Guo) by high performance liquid chromatography-triple quadrupole linear trap tandem mass spectrometry …
[cited by applicant]
Shiba et al., 2007, Engineering of the pyruvate dehydrogenase bypass in
[cited by applicant]
Shibuya et al., 2004, Cucurbitadienol synthase, the first committed enzyme for cucurbitacin biosyntheis, is a distinct enzyme from cycloartenol synthase for phytosterol biosynthesis, Tetrahedron 60:6995-7003.
[cited by applicant]
Su et al. Jul. 2017, Molecular and biochemical characterization of squalene synthase from Siraitia grosvenorii, Biotechnol Lett. vol. 39, Issue 7, pp. 1009-1018.
[cited by applicant]
Tai et al., 2013, Engineering the push and pull of lipid biosynthesis in oleaginous yeast Yarrowia lipolytica for biofuel production. Metab Eng, 15:1-9.
[cited by applicant]
Takase et al. 2015, Control of the 1,2-rearrangement process by oxidosqualene cyclases during triterpene biosynthesis, Org Biomol Chem. 13(26):7331-6.
[cited by applicant]
Takemoto et al., 1983, Studies on the constituents of fructus momordicae. III. Structure of mogrosides, Pharmaceutical Journal, 103(11):1167-1173.
[cited by applicant]
Tang et al., 2011, An efficient approach to finding siraitia grosvenorii triterpene biosynthetic genes by RNA-seq and digital gene expression analysis, BMC Genomics, 12:343.
[cited by applicant]
Thompson et al., 2014, Squalene production using saccharomyces cerevisiae, i-ACES, 1(1), 7 pp.
[cited by applicant]
Treisman et al., 1990, The SRE: a growth factor responsive transcriptional regulator, Seminars in Cancer Biol. 1:47-58.
[cited by applicant]
U.S. FDA list of Everything Added to Food in the U.S. (EAFUS), available at http://www.accessdata.fda.gov/scripts/fcn/fcnNavigation.cfm?rpt=eafusListing, last accessed Nov. 16, 2015, 186 pp.
[cited by applicant]
Wang et al., 2015, Hyperproduction of β-Glucanase Exg1 promotes the Bioconversion of mogrosides in
[cited by applicant]
Wang et al., 2019, Dekkera bruxellensis, a beer yeast that specifically bioconverts mogroside extracts into the intense natural sweetener siamensode I, Food Chemistry, 276:43-49.
[cited by applicant]
Wang et al., Aug. 20, 2014, Cucurbitane glycosides derived from mogroside IIE: structure-taste relationships, antioxidant activity, and acute toxicity, Molecules, 19(8):12676-12689.
[cited by applicant]
Westfall et al., 2012, Production of amorphadiene in yeast, and its conversion to dihydroartemisinic acid, precursor to the antimalarial agent artemisinin. Proc Natl Acad Sci U S A, 109:E111-118.
[cited by applicant]
Whisstock et al., 2003, Prediction of protein function from protein sequence and structure, Quarterly Review of Biophysics, 36(3):307-340.
[cited by applicant]
Wiet et al., 1993, Fat concentration affects sweetness and sensory profiles of sucrose, sucralose, and aspartame, J. Food Sci., 58(3):599-602.
[cited by applicant]
Witkowski et al., 1999, Conversion of a β-ketoacyl synthyase to a malonyl decarboxylase by replacement of the active-site cysteine with glutamine, Biochemistry, 38:11643-11650.
[cited by applicant]
Xu et al., 2015, Exploring in vitro, in vivo metabolism of mogroside V and distribution of its metabolites in rats by HPLC-ESI-IT-TOF-MS
[cited by applicant]
Yang et al., 2016, Metabolites of siamenoside I and their distributions in rats, Molecules, 21:1-20.
[cited by applicant]
Yang et al., Sep. 2005, Grosmomoside I, a new cucurbitane triterpenoid glycoside from fruits of momordica grosvenori, Chinese Traditional and Herbal Drugs, 36(9):1285-1290.
[cited by applicant]
Ye et al., 1994, Characterization of a Silencer Regulatory Element in the Human Interferon-y Promoter, J. Biol. Chem. 269:25728-25734.
[cited by applicant]
Zhang et al., 2012, Identification of flavonol and triperpene glycosides in Lui-Han-Guo extract using ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry, Journal of Food Compsition …
[cited by applicant]
Zhang et al., 2015, Functional pyruvate formate lyase pathway expressed with two different electron donors in
[cited by applicant]
Zhang et al., 2016, Oxidation of Cucurbitadienol Catalyzed by CYP87D18 in the Biosynthesis of Mogrosides from Siraitia grosvenoril. Plant Cell Physiol 57:1000-1007.
[cited by applicant]
Zhou et al., 2012, Enhanced alpha-ketoglutarate production in Yarrowia lipolytica WSH-Z06 by alteration of the acetyl-CoA metabolism. J Biotechnol, 161:257-264.
[cited by applicant]
Zhou et al., 2016, Comprehensive analysis of 61 characteristic constituents from siraitiae fructus using ultrahigh-pressure liquid chromatography with time-of-flight mass spectrometry, Journal of Pharmaceutical and Biom…
[cited by applicant]
Zhou et al., 2017, Biotransformation of total saponins in siraltia fructus by human intestinal microbiota of normal and type 2 diabetic patients: comprehensive metabolite identification and metabolic profile elucidation…
[cited by applicant]
International Search Report dated Nov. 14, 2018 in PCT/US16/030627.
[cited by applicant]
Chaturvedula et al., 2011, Cucurbitane glycosides form Siraitia grosvenorii, J. Carbohydr. Chem., 30(1):16-26.
[cited by applicant]
Perez Gutierrez, 2007, Triperpenes, in Handbook of Compounds with Cytotoxic Activity Isolated from Pants, Nova Science Publishers Inc., p. 511.
[cited by applicant]
Szarek et al., 1984, L-glucose. A convenient synthesis from D-glucose, Can. J. Chem., 62(4):671-674.
[cited by applicant]
Ahmad et al., Jun. 2000, Spectroscopic Data of Saponins, CRC-Press, pp. 963-965.
[cited by applicant]
CAS Registry No. 1126032-65-2, Entered STN: Mar. 24, 2009.
[cited by applicant]
CAS Registry No. 126105-11-1, Entered STN: Mar. 30, 1990.
[cited by applicant]
CAS Registry No. 126105-12-2, Entered STN: Mar. 30, 1990.
[cited by applicant]
CAS Registry No. 130567-83-8, Entered STN: Nov. 23, 1990.
[cited by applicant]
CAS Registry No. 1421942-59-7, Entered STN: Feb. 27, 2013.
[cited by applicant]
CAS Registry No. 1613527-65-3, Entered STN: Jul. 8, 2014.
[cited by applicant]
CAS Registry No. 1707161-17-8, Entered STN: May 18, 2015.
[cited by applicant]
CAS Registry No. 189307-15-1, Entered STN: May 30, 1997.
[cited by applicant]
CAS Registry No. 2096516-68-4, Entered STN: May 22, 2017.
[cited by applicant]
CAS Registry No. 88901-37-5, Entered STN: Nov. 16, 1984.
[cited by applicant]
CAS Registry No. 88901-41-1, Entered STN: Nov. 16, 1984.
[cited by applicant]
CAS Registry No. 88901-42-2, Entered STN: Nov. 16, 1984.
[cited by applicant]
CAS Registry No. 88901-43-3, Entered STN: Nov. 16, 1984.
[cited by applicant]
CAS Registry No. 88901-46-6, Entered STN: Nov. 16, 1984.
[cited by applicant]
CAS Registry No. 88915-64-4, Entered STN: Nov. 16, 1984.
[cited by applicant]
Chatzifragkou et al., 2021, Chapter 18: Analysis of carbohydrates and glycoconjugates in food by CE and HPLC, in Carbohydrate Analyais by Modern Liquid Phase Separation Techniques, El Rassi ed., Elsevier, pp. 815-842.
[cited by applicant]
Gunjal et al., 2020, Chapter 5: Pectinase in degradation of lignocellulosic wastes, in Enzymes in Degrataion of the Lignocellulosic Wastes, Springer, pp. 71-103.
[cited by applicant]
Izawa et al., 2010, 4.16. Human-environment interaction—taste, in Comprehensive Natural Products II, Mander et al., eds., Elsevier, pp. 631-671.
[cited by applicant]
Lim, 2012, Siraitia grosvenorii, in Edible Medicinal and Non-Medicinal Plants., vol. 2, Fruits, Springer, pp. 392-400.
[cited by applicant]
McMurry, 2015, 25-3 D,L Sugars, in Organic Chemistry, Cengage Learning, p. 839.
[cited by applicant]
Merino et al., 2007, Progress and challenges in enzyme development for biomass utilization, Adv Biochem Engin/Biotechnol, 108:105-120.
[cited by applicant]
Plou et al., 2007, Application of glycosidases and transglycosidases in the synthesis of oligosaccharides, in Industrial Enzymes: Structure, Function and applications, Polaina et al., eds., Springer, pp. 141-157.
[cited by applicant]
Schomburg et al., eds., 2006, Springer Handbook fo Enzymes, vol. 31, Sucrose synthase, 2.4.1.13, pp. 113-125.
[cited by applicant]
Schomburg et al., eds., 2006, Springer Handbook of Enzymes, vol. 31, Class 2, Transferases IV, Dextransucrase, 2.4.1.5, pp. 49-59.
[cited by applicant]
Shoda, Jul. 2001, Chapter 5.3.1: Enzymatic glycosylation, in Glycoscience; Chemistry and Chemical Biology I-III, Frasier-Reid et al., eds., Springer, pp. 1466-1496.
[cited by applicant]
Stoddart, 1984, Chapter 5. Polysaccharide assembly in eukaryotes, in The Biosynthesis of Polysaccharides, Croom Helm, London & Sydney, pp. 179-261.
[cited by applicant]
Veana et al., 2018, Chapter 10. Invertase: an enzyme with importance in confectionery food industry, in Enzymes in Food Technology, Kuddus ed., Springer, pp. 187-212.
[cited by applicant]
Wagner et al., eds., 2015, Fructus Siraitiae/Momordicase-Luohanguo, in Chromatographic Fingerprint Analysis of Herbal Medicines., vol. 3, Springer International Publishing Switzerland, pp. 197-198.
[cited by applicant]
Broun et al., 1998, Catalytic plasticity of fatty acid modification enzymes underlying chemical diversity of plant lipids, Science, 282:1315-1317.
[cited by applicant]
Dols et al., Apr. 1998, Characterization of the different dextransucrase activities excreted in glucose, fructose, or sucrose medium by Leuconostoc mesenteroides NRRL B-1299, Applied and Environmental Microbiology, 64(4…
[cited by applicant]
Gotoh, Jan. 5, 1992, Substrate recognition sites in cytochrome P450 family 2 (CYPB) proteins inferred from comparative analyses of amino acid and coding nucleotide sequence, The Journal of Biological Chemistry, 267(1):8…
[cited by applicant]
Seffernick et al., 2001, Melamine deaminase and atrazine chlorohydrolase: 98 percent identical but functionally difference, Journal of Bacteriology, 183(8):2405-2410.
[cited by applicant]
Uitdehaag et al., 2002, Catalytic mechanism and product specificity of cyclodextrin glycosytransferase, a prototypical transglycosylase from the a-amylase family, Enzyme and Microbial Technology, 30:195-304.
[cited by applicant]
Wang et al., Jan. 5, 2018, Biotransformation of mogrosides, Sweeteners, pp. 153-165.
[cited by applicant]
Xu et al., 2021, Selective enzymatic α-1,6-monoglucosylation of mogroside IIIE for the bio-creation of α-siamenoside I, a potential high-Intensity sweetener, Food Chemistry, 359:1-9.
[cited by applicant]
Brenda, Sequence of CDGT1-NIACI, EC No. 2.4.1.19, Jan. 2023.
[cited by applicant]
Zhou et al., Aug. 16, 2010, Enzymatic synthesis of α-glucosyl-timosaponin BII catalyzed by the extremely thermophilic enzyme: Toruzyme 3.0L, Carbohydrate Research, 345(12)1752-1759.
[cited by applicant]
Database GNPD [Online] Mintel; Aug. 1, 2019 (Aug. 1, 2019), anonymous: “Siraitia Grosvenorii Drink”, Database accession No. 6765873 Ingredients.
[cited by applicant]
Database GNPD [Online] Mintel; Apr. 11, 2019 (Apr. 11, 2019), anonymous: “Vanilla Flavor Whey Protein Dietary Supplement”, Database accession No. 6469573 Ingredients.
[cited by applicant]
Database GNPD [Online] Mintel; Nov. 11, 2020 (Nov. 11, 2020), anonymous: “Lemon-Lime BCAA + Creatine Perform Powder”, Database accession No. 8258975 Ingredients.
[cited by applicant]
Database GNPD [Online] Mintel; Jun. 14, 2019 (Jun. 14, 2019), anonymous: “Herbal Water”, Database accession No. 6637495 Ingredients.
[cited by applicant]
Database GNPD [Online] Mintel; Jul. 19, 2012 (Jul. 19, 2012), anonymous: “Natural Appetite Management Supplement Drink”, Database accession No. 1838679 Ingredients.
[cited by applicant]
Database GNPD [Online] Mintel; Sep. 28, 2020 (Sep. 28, 2020), anonymous: “Lemon Tea Drink with Stevia and Monk Fruit”, Database accession No. 8138517 Ingredients.
[cited by applicant]
Database GNPD [Online] Mintel; Mar. 9, 2020 (Mar. 9, 2020), anonymous: “Honeysuckle, Momordica Grosvenori and Snow Pear Black Tea”, Database accession No. 7425799 Ingredients.
[cited by applicant]
Database GNPD [Online] Mintel; Nov. 9, 2017 (Nov. 9, 2017), anonymous: “Vanilla Cold Brew Coffee”, XP055915994, Database accession No. 5227311 Ingredients.
[cited by applicant]
Wang et al., Sep. 2019, Analysis of mogrosides in siraitia grosvenorii fruits at different stages of maturity, Natural Product Communications, 14(1):1-5.
[cited by applicant]
Wang et al., 2019, Dekkera bruxellensis, a beer yeast that specifically bioconverts mogroside extracts into the intense natural sweetener siamensode I, Food Chemistry, supplementary data.
[cited by applicant]