Dicyclopropylmethyl peptide backbone protectant.
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 of Fmoc-(Dcpm)Gly-OH for Fmoc-Gly-OH in the assembly of sequences containing the sensitive Asp-Gly unit.
Carpino
Louis A
LA
Department of Chemistry, University of Massachusetts, Amherst, Massachusetts 01003, USA. carpino@chem.umass.edu
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
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
D000596:Amino Acids; D003521:Cyclopropanes; D004151:Dipeptides; D009842:Oligopeptides; C017033:aspartylglycine