Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group using HCL/dioxane (4 M)

G. Han; M. Tamaki; V. J. Hruby

doi:10.1034/j.1399-3011.2001.00935.x

Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group using HCL/dioxane (4 M)

G. Han, M. Tamaki, V. J. Hruby

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

130 Scopus citations

Abstract

Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group of various amino acids and peptides was achieved by using hydrogen chloride (4 M) in anhydrous dioxane solution for 30 min at room temperature. In the cases studied in our laboratory, this protocol provided superior selectivity to deprotect N^α-Boc groups in the presence of tert-butyl esters and tert-butyl ethers, including thio-tert-butyl ethers, but not phenolic tert-butyl ethers.

Original language	English (US)
Pages (from-to)	338-341
Number of pages	4
Journal	Journal of Peptide Research
Volume	58
Issue number	4
DOIs	https://doi.org/10.1034/j.1399-3011.2001.00935.x
State	Published - 2001
Externally published	Yes

Keywords

Boc
Dioxane
Hydrogen chloride
Selective deprotection
Tert-butyl ester

ASJC Scopus subject areas

Biochemistry
Endocrinology

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10.1034/j.1399-3011.2001.00935.x

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abstract = "Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group of various amino acids and peptides was achieved by using hydrogen chloride (4 M) in anhydrous dioxane solution for 30 min at room temperature. In the cases studied in our laboratory, this protocol provided superior selectivity to deprotect Nα-Boc groups in the presence of tert-butyl esters and tert-butyl ethers, including thio-tert-butyl ethers, but not phenolic tert-butyl ethers.",

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AU - Han, G.

AU - Tamaki, M.

AU - Hruby, V. J.

PY - 2001

Y1 - 2001

N2 - Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group of various amino acids and peptides was achieved by using hydrogen chloride (4 M) in anhydrous dioxane solution for 30 min at room temperature. In the cases studied in our laboratory, this protocol provided superior selectivity to deprotect Nα-Boc groups in the presence of tert-butyl esters and tert-butyl ethers, including thio-tert-butyl ethers, but not phenolic tert-butyl ethers.

AB - Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group of various amino acids and peptides was achieved by using hydrogen chloride (4 M) in anhydrous dioxane solution for 30 min at room temperature. In the cases studied in our laboratory, this protocol provided superior selectivity to deprotect Nα-Boc groups in the presence of tert-butyl esters and tert-butyl ethers, including thio-tert-butyl ethers, but not phenolic tert-butyl ethers.

KW - Boc

KW - Dioxane

KW - Hydrogen chloride

KW - Selective deprotection

KW - Tert-butyl ester

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JF - Journal of Peptide Research

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ER -

Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group using HCL/dioxane (4 M)

Abstract

Keywords

ASJC Scopus subject areas

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