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US 4,055,468 AGranted
Processes for producing physiologically active peptide and its N-acyl derivatives
AssigneeSanraku-Ocean Co., Ltd.
InventorsHamao Umezawa, Tomio Takeuchi, Takaaki Aoyagi, Akira Takamatsu, Taiji Inui, Hiroshi Tone, Hajime Morishima
Life of this patent
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Abstract
A novel physiologically active peptide Val--X--Ala--X, in which X is 4-amino-3-hydroxy-6-methylheptanoic acid, which is prepared from R--Val--Val--X--Ala--X by the action of a microbial enzyme, N-acyl derivatives thereof which are produced by acylating said new peptide, and the processes for producing thereof and the microbial enzyme are disclosed.
Claims6
A process for producing a tetrapeptide of the formula:
- Val--X--Ala--X,
- wherein Val is L-valine, X is amino-3-hydroxy-6-methylheptanoic acid or a salt or an ester thereof and Ala is L-alanine, and the carboxyl group of the X between Val and Ala being bound to the amino group of Ala to form a peptide bond and the amino group of the X between Val and Ala being bound to the carboxyl group of Val to form a peptide bond, the amino group of the other X being bound to the carboxyl group of Ala to form a peptide bond, and the carboxyl group of the other X being free or esterified or bound to a cation to form a salt
- which comprises decomposing an N-acyl peptide of the general formula:
- R--Val--Val--X--Ala--X,
- wherein Val, Ala and X are the same as previously defined, and R is an acyl radical having carbon atoms of 2 to 8 or an acyl radical partially substituted by one or more hydroxyl groups or halogen atoms or a C-terminal of an esterified carboxyl group, and the amino group of the Val adjacent to X being bound to the carboxyl group of the other Val to form a peptide bond and the carboxyl group of the R being bound to the amino group of the Val to form an amide bond,
- specifically to carboxylic acid, L-valine and and Val--X--Ala--X by contacting said N-acyl peptide with an enzyme produced by a microorganism.
3 more elements
A process for producing a N-acyl peptide of the tetrapeptide of the formula:
- R'--Val--X--Ala--X,
- wherein R' is an acyl radical having 1 to 16 carbon atoms or an acyl radical partially substituted by one or more hydroxyl groups or halogen atoms or a C-Terminal of an esterified carboxyl group and the carboxyl group of the R' being bound to the amino group of the Val to form an amide bond and the Val, Ala and X are the same as defined in claim 15
- which comprises decomposing an N-acyl peptide having the general formula,
- R--Val--Val--X--Ala--X,
- wherein R, Val, Ala and X are as defined in claim 1, specifically to carboxylic acid, L-valine and Val--X--Ala--X by contacting said N-acyl peptide with an enzyme produced by a microorganism and acylating the thus obtained Val--X--Ala--X.
2 more elements
Dependencies are inferred from the claim text.