Application of DEPBT on the synthesis of the protected dipeptides containing histidine with unprotected imidazole group by solution method

3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4 (3H)-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 st...

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Bibliographic Details
Published inChinese journal of chemistry Vol. 21; no. 7; pp. 801 - 804
Main Authors Shen, HY, Tian, GL, Zhu, WJ, Ha, S, Ye, YH
Format Journal Article
LanguageEnglish
Published MALDEN Wiley 01.07.2003
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
coupling reagent
peptide
PEPTIDE-SYNTHESIS
DERIVATIVES
histidine
DEPBT
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Summary:3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4 (3H)-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 acids, the yields were relatively high (63%-81%). However, when the carboxyl components were N-protected acidic amino acids, the yields were relatively low (47%-48%). The results expanded the application of DEPBT on the synthesis of bioactive peptides containing histidine.
ISSN:1001-604X
DOI:10.1002/cjoc.20030210718