Synthesis, solution structure and biological activity of Val-Val-Pro-Gln, a bioactive elastin peptide

Caterina Spezzacatena; Antonietta Pepe; Lora M. Green; Lawrence B. Sandberg; Brigida Bochicchio; Antonio M. Tamburro

doi:10.1002/ejoc.200400510

Synthesis, solution structure and biological activity of Val-Val-Pro-Gln, a bioactive elastin peptide

Caterina Spezzacatena
, Antonietta Pepe
, Lora M. Green
, Lawrence B. Sandberg
, Brigida Bochicchio
, Antonio M. Tamburro

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

Abstract

Val-Val-Pro-Gln (valyl-valyl-prolyl-glutamine) is a small but highly conserved sequence present in all elastins. We describe its synthesis by mixed anhydride solution chemistry as an alternative to solid-phase peptide synthesis (SPPS). The molecular structure of the tetrapeptide in solution was investigated by classical spectroscopy, such as circular dichroism (CD), nuclear magnetic resonance (NMR) and Fourier Transform Infrared Spectroscopy (FTIR). The biological activity of Val-Val-Pro-Gln was evaluated by a bromodeoxyuridine (BrdU) incorporation assay with normal human dermal fibroblasts. This small peptide may play a critical role in control of matrix metabolism through its release from the elastin polypeptide chain during periods of tissue breakdown and remodelling.

Original language	English
Pages (from-to)	1644-1651
Number of pages	8
Journal	European Journal of Organic Chemistry
Issue number	8
DOIs	https://doi.org/10.1002/ejoc.200400510
State	Published - Apr 15 2005

ASJC Scopus Subject Areas

Physical and Theoretical Chemistry
Organic Chemistry

Keywords

Biological activity
Elastin
Peptides

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abstract = "Val-Val-Pro-Gln (valyl-valyl-prolyl-glutamine) is a small but highly conserved sequence present in all elastins. We describe its synthesis by mixed anhydride solution chemistry as an alternative to solid-phase peptide synthesis (SPPS). The molecular structure of the tetrapeptide in solution was investigated by classical spectroscopy, such as circular dichroism (CD), nuclear magnetic resonance (NMR) and Fourier Transform Infrared Spectroscopy (FTIR). The biological activity of Val-Val-Pro-Gln was evaluated by a bromodeoxyuridine (BrdU) incorporation assay with normal human dermal fibroblasts. This small peptide may play a critical role in control of matrix metabolism through its release from the elastin polypeptide chain during periods of tissue breakdown and remodelling.",

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AU - Spezzacatena, Caterina

AU - Pepe, Antonietta

AU - Green, Lora M.

AU - Sandberg, Lawrence B.

AU - Bochicchio, Brigida

AU - Tamburro, Antonio M.

PY - 2005/4/15

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KW - Biological activity

KW - Elastin

KW - Peptides

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Synthesis, solution structure and biological activity of Val-Val-Pro-Gln, a bioactive elastin peptide

Abstract

ASJC Scopus Subject Areas

Keywords

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