One-Pot Peptide Ligation-Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides

Jan Spengler; Juan B. Blanco-Canosa; Luciano Forni; Fernando Albericio

doi:10.1021/acs.orglett.8b01741

One-Pot Peptide Ligation-Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides

Jan Spengler
, Juan B. Blanco-Canosa
, Luciano Forni
, Fernando Albericio

Life sciences Faculty

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

10 Scopus citations

Abstract

Native chemical ligation (NCL) employing the N-methylbenzimidazolinone (MeNbz) linker readily provided the linear precursor of a 16-mer peptide that is difficult to obtain by stepwise solid-phase peptide synthesis. NCL and the workup conditions were improved toward a protocol that allows for quantitative removal of the 4-hydroxymercaptophenol additive and subsequent formation of the disulfide bridge in the NCL cocktail by oxidation in air, tolerated by the presence of tris(hydroxypropyl)phosphine.

Original language	English
Pages (from-to)	4306-4309
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.8b01741
State	Published - 20 Jul 2018

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Copyright © 2018 American Chemical Society.

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title = "One-Pot Peptide Ligation-Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides",

abstract = "Native chemical ligation (NCL) employing the N-methylbenzimidazolinone (MeNbz) linker readily provided the linear precursor of a 16-mer peptide that is difficult to obtain by stepwise solid-phase peptide synthesis. NCL and the workup conditions were improved toward a protocol that allows for quantitative removal of the 4-hydroxymercaptophenol additive and subsequent formation of the disulfide bridge in the NCL cocktail by oxidation in air, tolerated by the presence of tris(hydroxypropyl)phosphine.",

author = "Jan Spengler and Blanco-Canosa, \{Juan B.\} and Luciano Forni and Fernando Albericio",

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T1 - One-Pot Peptide Ligation-Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides

AU - Spengler, Jan

AU - Blanco-Canosa, Juan B.

AU - Forni, Luciano

AU - Albericio, Fernando

PY - 2018/7/20

Y1 - 2018/7/20

N2 - Native chemical ligation (NCL) employing the N-methylbenzimidazolinone (MeNbz) linker readily provided the linear precursor of a 16-mer peptide that is difficult to obtain by stepwise solid-phase peptide synthesis. NCL and the workup conditions were improved toward a protocol that allows for quantitative removal of the 4-hydroxymercaptophenol additive and subsequent formation of the disulfide bridge in the NCL cocktail by oxidation in air, tolerated by the presence of tris(hydroxypropyl)phosphine.

AB - Native chemical ligation (NCL) employing the N-methylbenzimidazolinone (MeNbz) linker readily provided the linear precursor of a 16-mer peptide that is difficult to obtain by stepwise solid-phase peptide synthesis. NCL and the workup conditions were improved toward a protocol that allows for quantitative removal of the 4-hydroxymercaptophenol additive and subsequent formation of the disulfide bridge in the NCL cocktail by oxidation in air, tolerated by the presence of tris(hydroxypropyl)phosphine.

UR - https://www.scopus.com/pages/publications/85050241269

U2 - 10.1021/acs.orglett.8b01741

DO - 10.1021/acs.orglett.8b01741

M3 - Artículo

C2 - 29953237

AN - SCOPUS:85050241269

SN - 1523-7060

VL - 20

SP - 4306

EP - 4309

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

One-Pot Peptide Ligation-Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides

Abstract

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