通过对人类中性粒细胞的研究表明，HCO - 甲硫氨酸 - 亮氨酸 - 苯丙氨酸 - 甲酯类似物中第2位肽键的重要性。

The importance of the peptide bond at position 2 in HCO-Met-Leu-Phe-OMe analogues as shown by studies on human neutrophils.

作者信息

Cavicchioni G, Breveglieri A, Boggian M, Vertuani G, Reali E, Spisani S

机构信息

Department of Pharmaceutical Sciences, University of Ferrara, Italy.

出版信息

J Pept Sci. 1996 May-Jun;2(3):135-40. doi: 10.1002/psc.55.

DOI:10.1002/psc.55

PMID:9231322

Abstract

The formylpeptides formyl-methionyl-N-methylleucyl-phenylalanine methyl ester [for-Met-(NMe)Leu-Phe-OMe] 1, formyl-methionyl-2-aminotetralin-2-carboxyl-phenylalanine methyl ester [for-Met-Atc-Phe-OMe] 2, formyl-methionyl-1,2,3,4-tetrahydroisoquinoline-3-carboxyl-phenylalanine methyl ester [for-Met-Tic-Phe-OMe] 3 and formyl-methionyl-2-aminoxy-4-methylvaleryl-phenylalanine methyl ester [for-Met-OLeu-Phe-OMe] 4 were synthesized in order to investigate the role of the amide bond at position 2 on biological activities on human neutrophils. Only analogue 2, which keeps the NH group at position 2, was found to retain activity though sterically encumbered.

摘要

为了研究2位酰胺键对人中性粒细胞生物活性的作用，合成了甲酰肽甲酰 - 甲硫氨酰 - N - 甲基亮氨酰 - 苯丙氨酸甲酯[甲酰 - 蛋氨酸 -（N - 甲基）亮氨酸 - 苯丙氨酸甲酯][for - Met - (NMe)Leu - Phe - OMe]1、甲酰 - 甲硫氨酰 - 2 - 氨基四氢萘 - 2 - 羧基 - 苯丙氨酸甲酯[for - Met - Atc - Phe - OMe]2、甲酰 - 甲硫氨酰 - 1,2,3,4 - 四氢异喹啉 - 3 - 羧基 - 苯丙氨酸甲酯[for - Met - Tic - Phe - OMe]3和甲酰 - 甲硫氨酰 - 2 - 氨基氧基 - 4 - 甲基戊酰 - 苯丙氨酸甲酯[for - Met - OLeu - Phe - OMe]4。只有在2位保留NH基团的类似物2，尽管存在空间位阻，仍被发现保留活性。