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Application of DEPBT on the Synthesis of the Protected Dipeptides Containing Histidine with Unprotected Imidazole Group by Solution Method
Author(s) -
Shen HongYan,
Tian GuiLing,
Zhu WenJiang,
Ha Sha,
Ye YunHua
Publication year - 2003
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20030210718
Subject(s) - chemistry , imidazole , histidine , reagent , amino acid , protecting group , combinatorial chemistry , peptide synthesis , organic chemistry , biochemistry , alkyl
3‐(Diethoxyphosphoryloxy)‐1, 2, 3‐benzotriazin‐4(3 H )‐one (DEPBT) was an organophosphorus coupling reagent developed by our group. It was an effective coupling reagent for the synthesis of protected peptides containing Tyr, Ser and Thr with unprotected hydroxy group on their side chain. The further study of the synthesis of a series of protected dipeptides containing histidine with unprotected imidazole group using DEPBT is reported. During the synthetic procedure, the imidazole group of histidine did not need to be protected. When the carboxyl components were N ‐protected aromatic amino acids or basic amino adds, the yields were relatively high (63%—81%). However, when the carboxyl components were N ‐protected acidic amino adds, the yields were relatively low (47%—48%). The results expanded the application of DEPBT on the synthesis of bioactive peptides containing histidine.