Synthesis of dermorphin-(1-4) derivatives catalyzed by proteases in   organic solvents

doi:10.1111/j.1399-3011.2004.00198.x

CORC > 北京大学 > 化学与分子工程学院

	Synthesis of dermorphin-(1-4) derivatives catalyzed by proteases in organic solvents
	Shen, HY ; Tian, GL ; Ye, YH
刊名	journal of peptide research
	2005
关键词	D-amino acid dermorphin organic solvents peptide synthesis proteases ENZYMATIC-SYNTHESIS PEPTIDE-SYNTHESIS AMINO-ACIDS ALPHA-CHYMOTRYPSIN MEDIA SKIN PRECURSOR
DOI	10.1111/j.1399-3011.2004.00198.x
英文摘要	In order to extend the use of proteases to organic synthesis and seek the rules of enzymatic reactions in organic media, we focused on unnatural substrates for proteases to form amide bonds. In this paper, the study of unnatural substrates containing D-amino acid residue, which act as acyl acceptors as well as acyl donors for proteases in organic media, is reported. Dermorphin is a heptapeptide (H-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH(2)) with potent analgesic activity. The N-terminal tetrapeptide is the minimum sequence that retains dermorphin activity, and is selected as the model compound in our study. Two dermorphin-(1-4) derivatives, Boc-Tyr-D-Ala-Phe-Gly-N(2)H(2)Ph and Boc-Tyr-D-Ala-Phe-Gly-NH(2), which contained a D-amino acid residue, were synthesized by proteases in organic media for the first time. The synthesis of these two dermorphin-(1-4) derivatives could be catalyzed by subtilisin with Boc-Tyr-D-Ala-OCH(2)CF(3) as an acyl donor substrate in AcOEt. The synthesis of dermorphin-(1-2) derivative Boc-Tyr-D-Ala-N(2)H(2)Ph was catalyzed by alpha-chymotrypsin in different organic solvents and D-Ala-N(2)H(2)Ph was used as an acyl acceptor substrate. Factors influencing the above enzymatic reactions were systematically studied.; Biochemical Research Methods; Biochemistry & Molecular Biology; SCI(E); PubMed; 3; ARTICLE; 1; 143-148; 65
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/199489]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Shen, HY,Tian, GL,Ye, YH. Synthesis of dermorphin-(1-4) derivatives catalyzed by proteases in organic solvents[J]. journal of peptide research,2005.
APA	Shen, HY,Tian, GL,&Ye, YH.(2005).Synthesis of dermorphin-(1-4) derivatives catalyzed by proteases in organic solvents.journal of peptide research.
MLA	Shen, HY,et al."Synthesis of dermorphin-(1-4) derivatives catalyzed by proteases in organic solvents".journal of peptide research (2005).