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^*

^*Corresponding author for this work

Department of Chemistry and Biochemistry

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

132 Citations (Scopus)

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
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
Publication status	Published - 2001
Externally published	Yes

Keywords

Boc
Dioxane
Hydrogen chloride
Selective deprotection
Tert-butyl ester

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10.1034/j.1399-3011.2001.00935.x

Cite this

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AU - Tamaki, M.

AU - Hruby, V. J.

PY - 2001

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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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ER -

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

Abstract

Keywords

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