Compounds, compositions and use
A peptide comprising a unit of formula (I) and having a molecular weight of less than 2000 wherein each X is independently an organic group, e.g. a C 1-6 alkyl or C 1-6 alkenyl group, preferably —CH 2 —CH═CH 2 , or the two X groups taken together can form a covalent or non-covalent link between the two O groups, preferably a C 1-10 saturated or unsaturated carbon chain optionally interrupted by one or more heteroatoms selected from O, S, N, P, or Si, especially a C 3-10 carbon chain or one X represents an azido group and the other an C2-6-alkynyl group; both Z's are the same and are O or S; each Y is independently C, CH, CH 2 , N or NH; R 1 is H or C 1-6 alkyl; R 2 is H or C 1-6 alkyl; R 5 is a C 1-6 alkyl group, preferably isopropyl; or a salt, ester or prodrug thereof.
1. A peptide comprising a unit of formula (II)
wherein each X is independently a C 1-6 alkyl or C 2-6 alkenyl group, or the two X groups taken together form a covalent or non-covalent link between the two O groups, which is a C 1-10 saturated or unsaturated carbon chain optionally interrupted by one or more heteroatoms selected from O, S, N, P, or Si, or one X represents an azido group and the other an C 2-6 -alkynyl group;
each Y is independently C, CH, CH 2 , N or NH;
R 1 is H or C 1-6 alkyl;
R 2 is H or C 1-6 alkyl;
R 5 is a C 1-6 alkyl group;
R 3 and R 4 are protective groups for carboxylic groups or amino groups respectively, fluorescent probes, radiolabeled groups or a further peptide chain with 1-20 amino acids in the chain, the end groups of which optionally carry protective groups for carboxylic groups or amino groups respectively, fluorescent probes, or radiolabeled groups;
or a salt of the peptide.
2. The peptide as claimed in claim 1 of formula A:
wherein each X is independently a C 1-6 alkyl or C 2-6 alkenyl group, or wherein the two X groups taken together form a covalent or non-covalent link between the two O groups, which is a C 1-10 saturated or unsaturated carbon chain optionally interrupted by one or more heteroatoms selected from O, S, N, P, or Si;
each Y is independently C or N, optionally comprising hydrogen to satisfy the valency of the atom;
each R 1 is independently C 1-6 alkyl or hydrogen;
each R 2 is independently C 1-6 alkyl or hydrogen; and
R 3 and R 4 are protective groups for carboxylic groups or amino groups respectively, fluorescent probes, radiolabeled groups or peptide chains with 1-20 amino acids in the chain.
3. The peptide as claimed in claim 1 , wherein the two X groups taken together form a saturated or unsaturated C3-10 carbon chain between the two O atoms.
4. The peptide as claimed in claim 1 , wherein all Y groups are C.
5. The peptide as claimed in claim 1 , wherein R 1 is isopropyl and R 2 is H, or R 1 is H and R 2 is isopropyl, or R 1 =R 2 =methyl.
6. The peptide as claimed in claim 1 , wherein R 3 is a C-terminus peptide protecting group.
7. The peptide as claimed in claim 1 , wherein R 4 is a N-terminus peptide protecting group.
8. The peptide as claimed in claim 1 , wherein R 4 represents an addition amino acid chain of 1 to 5 units terminated by a peptide protecting group.
9. The peptide as claimed in claim 8 , wherein said chain is R 4 -Pro-Pro and R 4 is a protecting group.
10. The peptide as claimed in claim 1 of one of the following:
11. A pharmaceutical composition comprising a peptide as claimed in claim 1 along with at least one pharmaceutically acceptable excipient.
12. The peptide as claimed in claim 1 , wherein each X is —CH 2 —CH═CH 2 .
13. The peptide as claimed in claim 1 , wherein R 5 is isopropyl.
14. The peptide as claimed in claim 1 , wherein R 4 is butyloxycarbonyl (Boc).
15. The peptide as claimed in claim 1 , wherein the two X groups taken together form —CH 2 CH═CHCH 2 — or —CH 2 CH 2 CH 2 CH 2 —.
16. The peptide as claimed in claim 1 , wherein R 3 is a methyl ester.