胰蛋白酶抑制剂的研究。第三部分。猪胰分泌性胰蛋白酶抑制剂II（卡扎尔型）的保护十肽（序列15 - 24）的合成。

Studies on trypsin inhibitors. Part III. Synthesis of the protected decapeptide (sequence 15-24) of porcine pancreatic secretory trypsin inhibitor II (Kazal).

作者信息

Tomatis R, Guggi A, Ferroni R, Rocchi R

出版信息

Int J Pept Protein Res. 1976;8(1):87-95.

Abstract

The synthesis of the amino-protected decapeptide tert-butyloxycarbonylhydrazide corresponding to positions 15-24 of the amino acid sequence of porcine pancreatic secretory trypsin inhibitor II (Kazal inhibitor) is described. The tripeptide free base threonyl-beta-tert-butylaspartylglycine tert-butyloxycarbonylhydrazide (sequence 22-24) was acylated with 1-succinimidyl o-nitrophenylsulfenylvalyl-S-acetamidomethylcysteinylglycinate (sequence 19-21). Removal of the amino protecting group from the resulting hexapeptide followed by acylation of the free base with either benzyloxycarbonylisoleucyl-O-tert-butyltyrosylasparaginylproline or O-nitrophenylsulfenylisoleucyl-O-tert-butyltyrosylasparaginylproline, via the pyrazoline active ester method, yielded the decapeptide tert-butyloxycarbonylhydrazide (sequence 15-24) in the form of Nalpha-benzyloxycarbonyl or Nalpha-O-nitrophenylsulfenyl derivative. The stereochemical homogeneity of the two decapeptides was assessed, after partial deprotection with liquid hydrogen fluoride, or thioacetamide and aqueous 90% trifluoroacetic acid, by digestion with papain and aminopeptidase M followed by quantitative amino acid analysis.

摘要

本文描述了与猪胰分泌型胰蛋白酶抑制剂II（卡扎尔抑制剂）氨基酸序列第15 - 24位相对应的氨基保护十肽叔丁氧羰基酰肼的合成。用1 - 琥珀酰亚胺基邻硝基苯硫基缬氨酰 - S - 乙酰氨基甲基半胱氨酰甘氨酸酯（序列19 - 21）对三肽游离碱苏氨酰 - β - 叔丁基天冬氨酰甘氨酸叔丁氧羰基酰肼（序列22 - 24）进行酰化。从所得六肽中除去氨基保护基团，然后通过吡唑啉活性酯法用苄氧羰基异亮氨酰 - O - 叔丁基酪氨酰天冬酰胺基脯氨酸或邻硝基苯硫基异亮氨酰 - O - 叔丁基酪氨酰天冬酰胺基脯氨酸对游离碱进行酰化，得到Nα - 苄氧羰基或Nα - O - 邻硝基苯硫基衍生物形式的十肽叔丁氧羰基酰肼（序列15 - 24）。在用液态氟化氢或硫代乙酰胺和90%三氟乙酸水溶液进行部分脱保护后，通过用木瓜蛋白酶和氨肽酶M消化，随后进行定量氨基酸分析，评估了这两种十肽的立体化学均一性。

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