2-amino-3-methyl-hex-5-enoic acid and its use in the production of peptides including bacitracins
The present invention concerns 2-amino-3-methyl-hex-5-enoic acid, its use for the production of peptides such as bacitracins and a method for producing it.
1. The compound 2-amino-3-methyl-hex-5-enoic acid.
2. A compound according to claim 1 having (2S,3S) configuration.
3. A compound according to claim 1 having (2R,3S) configuration.
4. A compound according to claim 1 having (2S,3R) configuration.
5. A compound according to claim 1 having (2R,3R) configuration.
6. A method of producing a compound according to claim 1 , comprising a cross coupling of a vinyl Grignard agent with valine having a halide in 4-position.
7. The method according to claim 6 , where the cross coupling is catalyzed by Li 2 CuCl 4 .
8. A method of producing a compound according to claim 1 , comprising the following steps:
(a) coupling a vinyl Grignard reagent with 4-Iodo-N-phathaloylvaline methyl ester to form 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-methyl-hex-5-enoic acid methyl ester,
(b) cleaving the methyl ester moiety to generate the corresponding carboxylic acid; and
(c) deprotecting the alpha-amino group of 2-amino-3-methyl-hex-5-enoic acid.