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Lipidation of Cysteine or Cysteine‐Containing Peptides Using the Thiol‐Ene Reaction (CLipPA)
Author(s) -
Yang SungHyun,
Harris Paul W. R.,
Williams Geoffrey M.,
Brimble Margaret A.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501375
Subject(s) - cysteine , chemistry , thiol , peptide , residue (chemistry) , lipid anchored protein , ene reaction , coupling reaction , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , catalysis , enzyme , apoptosis , autophagy
The efficient synthesis of N α ‐protected S ‐palmitoylated cysteine building blocks using thiol‐ene coupling is described. These building blocks were incorporated into a resin‐bound peptide under racemisation‐suppressing conditions, and the degree of racemisation during the coupling process was assessed. The direct conjugation of vinyl palmitate with the sulfhydryl side‐chain of a cysteine residue on a semiprotected peptide was also studied. The reaction gave both mono‐ and bispalmitoylated cysteine residues in varying proportions, depending on the reaction conditions adopted.