https://www.amjmed.com/article/0002-9343(67)90087-3/pdf

Chemistry and structure-activity relations of the antidiuretic hormones

A list of amino‐acid derivatives which are useful in peptide synthesis

Syntheses and LH- and FSH-RH activities of LH-RH analogs substituted at position 8

A supplementary list of amino-acid derivatives which are useful in peptide synthesis.

l-Nω-Nitroarginine and l-arginine were coupled with N-(Cbz-α-aminoacyl)benzotriazoles and N-Cbz-dipeptidoylbenzotriazoles to provide arginine ll-dipeptides 9a−e, 11a−d; lll-tripeptides 18a−c, 20; and diastereomeric mixtures (9b+9b′), (9c+9c′), (11b+11b′) and (18c+18c′) [compound numbers written within parentheses represent a diastereomeric mixture or racemate; compound numbers without parentheses represent an achiral compound or a single enantiomer] by extension at the N-terminus of arginine, in isolated yields of 66−95% with complete retention of chirality as evidenced by NMR and HPLC analysis. Arginine ll-dipeptides 15a−d were synthesized by extension at the C-terminus of arginine in isolated yield of 66−80%, using benzotriazole activated arginine l-ωNO2-Arg-Bt, 13. Our methodology has also been used to synthesize the protected RGD peptide (Cbzα-l-ωNO2-Arg-Gly-l-Asp-(OH)2) 21.

H. G. Garg

Papers

1259. Amino-acids and peptides. Part XXIII. The synthesis of peptides related to arginine-vasopressin

Amino-acids and peptides. 23. The synthesis of peptides related to arginine-vasopressin.