Side reaction withN-carboxymethyl amino acids in the synthesis of backbone cyclized peptides

Autor:	Siegmund Reissmann, Diana Besser, Georg Greiner
Rok vydání:	1998
Předmět:	chemistry.chemical_classification Stereochemistry Pharmacology toxicology Side reaction food and beverages Bioengineering Biochemistry Analytical Chemistry Amino acid chemistry.chemical_compound Aminolysis chemistry Intramolecular force Drug Discovery Lactam Molecular Medicine
Zdroj:	Letters in Peptide Science. 5:299-303
ISSN:	1573-3904 0929-5666
DOI:	10.1007/bf02443547
Popis:	The use of N-carboxymethyl amino acids in the assembly of peptides with backbone cyclization can lead to diketopiperazine formation by intramolecular aminolysis which occurs despite the tert-butyl protection of the carboxy group. This undesired side reaction can be prevented by a very short deprotection time for the Fmoc group, by elongation of the N-carboxyalkyl chain or by forming the backbone (lactam) bridge before Fmoc removal, but not by the use of DBU or additives.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ab7c0fbee26264199ee24aecf2265517 https://doi.org/10.1007/bf02443547 Zobrazit plný text záznamu Full text from SpringerLink