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

Giorgio Cavicchioni; Angela Breveglieri; Marisa Boggian; Gianni Vertuani; Eva Reali; Susanna Spisani

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

Giorgio Cavicchioni, Angela Breveglieri, Marisa Boggian, Gianni Vertuani, Eva Reali, Susanna Spisani

IRCCS Istituto Ortopedico Galeazzi

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	135-140
Number of pages	6
Journal	Journal of Peptide Science
Volume	2
Issue number	3
Publication status	Published - May 1996

Keywords

Chemotaxis
Human neutrophils
Lysozyme release
N-formylmethionyl peptides
Superoxide anion generation

ASJC Scopus subject areas

Biochemistry, Genetics and Molecular Biology(all)
Biochemistry
Analytical Chemistry

Cite this

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title = "The Importance of the peptide bond at position 2 in HCO-Met-Leu-Phe-OMe analogues as shown by studies on human neutrophils",

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.",

keywords = "Chemotaxis, Human neutrophils, Lysozyme release, N-formylmethionyl peptides, Superoxide anion generation",

author = "Giorgio Cavicchioni and Angela Breveglieri and Marisa Boggian and Gianni Vertuani and Eva Reali and Susanna Spisani",

year = "1996",

month = may,

language = "English",

volume = "2",

pages = "135--140",

journal = "Journal of Peptide Science",

issn = "1075-2617",

publisher = "John Wiley and Sons Ltd",

number = "3",

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T1 - The Importance of the peptide bond at position 2 in HCO-Met-Leu-Phe-OMe analogues as shown by studies on human neutrophils

AU - Cavicchioni, Giorgio

AU - Breveglieri, Angela

AU - Boggian, Marisa

AU - Vertuani, Gianni

AU - Reali, Eva

AU - Spisani, Susanna

PY - 1996/5

Y1 - 1996/5

N2 - 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.

AB - 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.

KW - Chemotaxis

KW - Human neutrophils

KW - Lysozyme release

KW - N-formylmethionyl peptides

KW - Superoxide anion generation

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VL - 2

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EP - 140

JO - Journal of Peptide Science

JF - Journal of Peptide Science

SN - 1075-2617

IS - 3

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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