Dicyclopropylmethyl peptide backbone protectant.
Ontology highlight
ABSTRACT:
SUBMITTER: Carpino LA
PROVIDER: S-EPMC2811875 | biostudies-literature | 2009 Aug
REPOSITORIES: biostudies-literature
Publications
Dicyclopropylmethyl peptide backbone protectant.
Carpino Louis A LA Nasr Khaled K Abdel-Maksoud Adel Ali AA El-Faham Ayman A Ionescu Dumitru D Henklein Peter P Wenschuh Holger H Beyermann Michael M Krause Eberhard E Bienert Michael M
Organic letters 20090801 16
The N-dicyclopropylmethyl (Dcpm) residue, introduced into amino acids via reaction of dicyclopropylmethanimine hydrochloride with an amino acid ester followed by sodium cyanoborohydride or triacetoxyborohydride reduction, can be used as an amide bond protectant for peptide synthesis. Examples which demonstrate the amelioration of aggregation effects include syntheses of the alanine decapeptide and the prion peptide (106-126). Avoidance of cyclization to the aminosuccinimide followed substitution ...[more]
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