Thiazolidine-Protected β-Thiol Asparagine: Applications in One-Pot Ligation-Desulfurization Chemistry

Jessica Sayers; Robert E. Thompson; Kristen J. Perry; Lara R. Malins; Richard J. Payne

doi:10.1021/acs.orglett.5b02468

Thiazolidine-Protected β-Thiol Asparagine: Applications in One-Pot Ligation-Desulfurization Chemistry

Jessica Sayers, Robert E. Thompson, Kristen J. Perry, Lara R. Malins, Richard J. Payne^*

^*Corresponding author for this work

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

35 Citations (Scopus)

Abstract

The synthesis of a β-thiol asparagine derivative bearing a novel (2,4,6-trimethoxyphenyl)thiazolidine protecting group is described. The efficient incorporation of the amino acid into the N-termini of peptides is demonstrated as well as the utility of the β-thiol asparagine moiety for rapid ligation reactions with peptide thioesters. The streamlined synthesis of native peptide products could be accomplished using a one-pot radical desulfurization of the β-thiol auxiliary following the ligation event. The utility of the amino acid is highlighted in the efficient one-pot assembly of the HIV entry inhibitor enfuvirtide.

Original language	English
Pages (from-to)	4902-4905
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.5b02468
Publication status	Published - 2 Oct 2015
Externally published	Yes

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title = "Thiazolidine-Protected β-Thiol Asparagine: Applications in One-Pot Ligation-Desulfurization Chemistry",

abstract = "The synthesis of a β-thiol asparagine derivative bearing a novel (2,4,6-trimethoxyphenyl)thiazolidine protecting group is described. The efficient incorporation of the amino acid into the N-termini of peptides is demonstrated as well as the utility of the β-thiol asparagine moiety for rapid ligation reactions with peptide thioesters. The streamlined synthesis of native peptide products could be accomplished using a one-pot radical desulfurization of the β-thiol auxiliary following the ligation event. The utility of the amino acid is highlighted in the efficient one-pot assembly of the HIV entry inhibitor enfuvirtide.",

author = "Jessica Sayers and Thompson, {Robert E.} and Perry, {Kristen J.} and Malins, {Lara R.} and Payne, {Richard J.}",

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AU - Sayers, Jessica

AU - Thompson, Robert E.

AU - Perry, Kristen J.

AU - Malins, Lara R.

AU - Payne, Richard J.

PY - 2015/10/2

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AB - The synthesis of a β-thiol asparagine derivative bearing a novel (2,4,6-trimethoxyphenyl)thiazolidine protecting group is described. The efficient incorporation of the amino acid into the N-termini of peptides is demonstrated as well as the utility of the β-thiol asparagine moiety for rapid ligation reactions with peptide thioesters. The streamlined synthesis of native peptide products could be accomplished using a one-pot radical desulfurization of the β-thiol auxiliary following the ligation event. The utility of the amino acid is highlighted in the efficient one-pot assembly of the HIV entry inhibitor enfuvirtide.

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EP - 4905

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Thiazolidine-Protected β-Thiol Asparagine: Applications in One-Pot Ligation-Desulfurization Chemistry

Abstract

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