Strigolactone Compositions And Uses Thereof
Disclosed herein plant propagation materials, methods of manufacturing, formulations and uses thereof. The plant propagation materials disclosed herein may comprise a strigolactone obtained by a biosynthetic process. The plant propagation material may comprise a chemical mimic of a strigolactone. The strigolactone may be 5-deoxystrigol. Methods of manufacturing the plant propagation materials may comprise a chemical process. Alternatively, methods of manufacturing the plant propagation material may comprise a biosynthetic process. The methods may comprise use of one or more polynucleotides. The polynucleotides may encode a metabolite. The polynucleotides may comprise one or more genes encoding one or more components of a strigolactone pathway.
1 . A compound of Formula (I), a salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer thereof:
wherein:
a, c are each independently 0, 1, or 2;
b is 1 or 2;
each A is independently O, or S;
each E is independently O, S, or —NR 18 ;
each G is independently C;
R 5 , R 6 , R 11 , R 12 , R 14 , R 15 and R 17 are each independently H, alkyl, haloalkyl, amino, halo, or —OR 18 ;
R 2 , R 3 , R 7 , R 8 , R 9 , and R 10 are each independently H, alkyl, haloalkyl, amino, halo, —OR 18 or a lone electron pair;
R 1 and R 16 are each independently H, alkyl, haloalkyl, amino, halo, or —OR 18 ; or R 1 and R 16 together form a direct bond to provide a double bond;
R 4 and R 13 are each independently H, alkyl, haloalkyl, amino, halo, or —OR 18 ; or R 4 and R 13 together form a direct bond to provide a double bond;
each R 18 is independently H, alkyl, haloalkyl, aryl, heteroaryl, —C(O)R 19 or
and
each R 19 is independently H, alkyl, haloalkyl, aryl, or heteroaryl.
2 . A compound of Formula (II), a salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer thereof:
wherein:
a, c are each independently 0, 1, or 2;
b is 1 or 2:
each A is independently O, or S;
each E is independently O, S, or —NR 18 ;
each G is independently C;
R 5 , R 6 , R 11 , R 12 , R 14 , R 15 and R 17 are each independently H, alkyl, haloalkyl, amino, halo, or —OR 18 ;
R 2 , R 3 , R 7 , R 8 , R 9 , and R 10 are each independently H, alkyl, haloalkyl, amino, halo, —OR 18 or a lone electron pair;
R 1 and R 16 are each independently H, alkyl, haloalkyl, amino, halo, or —OR 18 ; or R 1 and R 16 together form a direct bond to provide a double bond;
R 4 and R 13 are each independently H, alkyl, haloalkyl, amino, halo, or —OR 18 ; or R 4 and R 13 together form a direct bond to provide a double bond;
each R 18 is independently H, alkyl, haloalkyl, aryl, heteroaryl, —C(O)R 19 or
and
each R 19 is independently H, alkyl, haloalkyl, aryl, or heteroaryl.
3 . The compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein a is 1, b is 2, c is 0.
4 . The compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein each A is independently O.
5 . The compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein each E is independently O.
6 . (canceled)
7 . The compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 16 are each independently H.
8 . The compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein R 1 , R 5 , R 6 , R 13 , and R 17 are each independently alkyl.
9 . The compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 8 , wherein R 1 , R 5 , R 6 , R 13 , and R 17 are each independently methyl.
10 . The compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 9 , having the structure of Formula (III):
11 . The compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 9 , having the structure of Formula (IV):
12 . The compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein the compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer has a diastereomeric excess of at least about 50%.
13 . A formulation comprising the compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 1 .
14 - 21 . (canceled)
22 . A method comprising contacting a plant with the compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 1 or the formulation of claim 13 .
23 - 51 . (canceled)
52 . A method of making a formulation comprising forming the formulation with the compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 1 .
53 - 54 . (canceled)
55 . A method of producing the compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 1 comprising alkylating
or a salt thereof, wherein R 17 is H, alkyl, halo, or haloalkyl and X is Cl, Br, or L.
56 - 67 . (canceled)
68 . An engineered cell comprising a plurality of polynucleotides, wherein (i) the plurality of polynucleotides encode one or more metabolites; and/or (ii) the plurality of polynucleotides comprise one or more heterologous genes selected from a group comprising crtE, crtB, crtI, D27, CCD7, CCD8, and MAXI.
69 - 76 . (canceled)
77 . The compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein in the moiety:
the stereocenter * is selected from the group consisting of: (S), (R), racemic, and a non-racemic mixture of (R) and (S).
78 . The compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 10 or 11 , wherein in the moiety:
the stereocenter * is selected from the group consisting of: (S), (R), racemic, and a non-racemic mixture of (R) and (S).
79 . A plant, food, or seed comprising the compound, salt, solvate, polymorph, diastereoisomer, stereoisomer, or isomer of claim 1 or the formulation of claim 13 .