Azo cyclization: Peptide cyclization via azo bridge formation

G. Fridkin; Chaim Gilon

doi:10.1034/j.1399-3011.2002.02993_1.x

Azo cyclization: Peptide cyclization via azo bridge formation

G. Fridkin, Chaim Gilon^*

^*Corresponding author for this work

Institute of Chemistry

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

21 Scopus citations

Abstract

A novel method for peptide cyclization in solution: the azo cyclization is presented herein. Ring closure by forming an azo bridge was achieved in situ by connecting the corresponding side chains of para amino phenylalanine (Pap) residues to those of tyrosine or histidine residues present in the corresponding linear precursors. The reaction was performed using an initial diazotization step in acidic media followed by intramolecular azo cyclization in a mild basic media. This new method of cyclization is facile, applicable to various sequences and results in a high yield of pure products and hence is suggested as an additional method for peptide cyclization. Here we report the successful utilization of this method for the synthesis of 10 new cyclic azo peptides, derived from RGD, GnRH, Tuftsin, VIP and SV40 NLS.

Original language	English
Pages (from-to)	104-111
Number of pages	8
Journal	Journal of Peptide Research
Volume	60
Issue number	2
DOIs	https://doi.org/10.1034/j.1399-3011.2002.02993_1.x
State	Published - 2002

Keywords

Azo cyclization
Cyclic azo GnRH
Cyclic azo RGD
Cyclic azo SV40 NLS
Cyclic azo Tuftsin
Cyclic azo VIP
Cyclic azo peptides

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10.1034/j.1399-3011.2002.02993_1.x

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title = "Azo cyclization: Peptide cyclization via azo bridge formation",

abstract = "A novel method for peptide cyclization in solution: the azo cyclization is presented herein. Ring closure by forming an azo bridge was achieved in situ by connecting the corresponding side chains of para amino phenylalanine (Pap) residues to those of tyrosine or histidine residues present in the corresponding linear precursors. The reaction was performed using an initial diazotization step in acidic media followed by intramolecular azo cyclization in a mild basic media. This new method of cyclization is facile, applicable to various sequences and results in a high yield of pure products and hence is suggested as an additional method for peptide cyclization. Here we report the successful utilization of this method for the synthesis of 10 new cyclic azo peptides, derived from RGD, GnRH, Tuftsin, VIP and SV40 NLS.",

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AB - A novel method for peptide cyclization in solution: the azo cyclization is presented herein. Ring closure by forming an azo bridge was achieved in situ by connecting the corresponding side chains of para amino phenylalanine (Pap) residues to those of tyrosine or histidine residues present in the corresponding linear precursors. The reaction was performed using an initial diazotization step in acidic media followed by intramolecular azo cyclization in a mild basic media. This new method of cyclization is facile, applicable to various sequences and results in a high yield of pure products and hence is suggested as an additional method for peptide cyclization. Here we report the successful utilization of this method for the synthesis of 10 new cyclic azo peptides, derived from RGD, GnRH, Tuftsin, VIP and SV40 NLS.

KW - Azo cyclization

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KW - Cyclic azo peptides

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Azo cyclization: Peptide cyclization via azo bridge formation

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