p-Nitromandelic acid as a highly acid-stable safety-catch linker for solid-phase synthesis of peptide and depsipeptide acids

Albert Isidro-Llobet; Mercedes Alvarez; Klaus Burger; Jan Spengler; Fernando Albericio

doi:10.1021/ol063148h

p-Nitromandelic acid as a highly acid-stable safety-catch linker for solid-phase synthesis of peptide and depsipeptide acids

Albert Isidro-Llobet
, Mercedes Alvarez
, Klaus Burger
, Jan Spengler
, Fernando Albericio

University of Barcelona
Leipzig University

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

11 Scopus citations

Abstract

Equation presented p-Nitromandelic acid as a safety-catch linker for Boc/Bzl-SPPS of base-labile compounds like peptides and depsipeptides is described. This linker permits acidic removal of side-chain protection groups from the resin. For cleavage from the solid support, the p-nitro group was reduced with tin(II) chloride. After washing off the reducing agents, the (depsi)peptide acids with or without the side-chain protection schemes were obtained by microwave irradiation at 50°C with 5% TFA in dioxane.

Original language	English
Pages (from-to)	1429-1432
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	8
DOIs	https://doi.org/10.1021/ol063148h
State	Published - 12 Apr 2007
Externally published	Yes

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10.1021/ol063148h

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abstract = "Equation presented p-Nitromandelic acid as a safety-catch linker for Boc/Bzl-SPPS of base-labile compounds like peptides and depsipeptides is described. This linker permits acidic removal of side-chain protection groups from the resin. For cleavage from the solid support, the p-nitro group was reduced with tin(II) chloride. After washing off the reducing agents, the (depsi)peptide acids with or without the side-chain protection schemes were obtained by microwave irradiation at 50°C with 5\% TFA in dioxane.",

author = "Albert Isidro-Llobet and Mercedes Alvarez and Klaus Burger and Jan Spengler and Fernando Albericio",

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T1 - p-Nitromandelic acid as a highly acid-stable safety-catch linker for solid-phase synthesis of peptide and depsipeptide acids

AU - Isidro-Llobet, Albert

AU - Alvarez, Mercedes

AU - Burger, Klaus

AU - Spengler, Jan

AU - Albericio, Fernando

PY - 2007/4/12

Y1 - 2007/4/12

N2 - Equation presented p-Nitromandelic acid as a safety-catch linker for Boc/Bzl-SPPS of base-labile compounds like peptides and depsipeptides is described. This linker permits acidic removal of side-chain protection groups from the resin. For cleavage from the solid support, the p-nitro group was reduced with tin(II) chloride. After washing off the reducing agents, the (depsi)peptide acids with or without the side-chain protection schemes were obtained by microwave irradiation at 50°C with 5% TFA in dioxane.

AB - Equation presented p-Nitromandelic acid as a safety-catch linker for Boc/Bzl-SPPS of base-labile compounds like peptides and depsipeptides is described. This linker permits acidic removal of side-chain protection groups from the resin. For cleavage from the solid support, the p-nitro group was reduced with tin(II) chloride. After washing off the reducing agents, the (depsi)peptide acids with or without the side-chain protection schemes were obtained by microwave irradiation at 50°C with 5% TFA in dioxane.

UR - https://www.scopus.com/pages/publications/34247540455

U2 - 10.1021/ol063148h

DO - 10.1021/ol063148h

M3 - Artículo

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JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

p-Nitromandelic acid as a highly acid-stable safety-catch linker for solid-phase synthesis of peptide and depsipeptide acids

Abstract

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