ISSN:
1434-4475
Keywords:
Activation, lactam-formation, side-reactions
;
N7,N8-(1,2-Dihydroxycyclohex-1,2-ylen)-arginine-derivatives and -peptides
;
Semisynthesis
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract A method for the synthesis of arginine peptides is described, in which the side chain guanidine function is blocked through reaction with 1,2-cyclohexanedione in borate buffers. Coupling to the carboxyl group of arginine was achieved by active ester, by dicyclohexylcarbodiimide/1-hydroxybenzotriazole1, and by the mixed anhydride methods2. Neither lactam formation nor acylation of the vicinal hydroxyls of the N7, N8-(1,2-dihydroxycyclohex-1,2-ylene) guanidino group was observed. Removal of the protecting group is strongly influenced by steric factors. Some side reactions observed during modification of peptides and protein fragments with 1,2-cyclohexanedione are also described.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00799922
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