Studies related to the relative thermodynamic stability of C-terminal peptidyl esters of O-hydroxy thiophenol: Emergence of a doable strategy for non-cysteine ligation applicable to the chemical synthesis of glycopeptides

Gong Chen; J. David Warren; Jiehao Chen; Bin Wu; Qian Wan; Samuel J. Danishefsky

doi:10.1021/ja061588y

Studies related to the relative thermodynamic stability of C-terminal peptidyl esters of O-hydroxy thiophenol: Emergence of a doable strategy for non-cysteine ligation applicable to the chemical synthesis of glycopeptides

Gong Chen, J. David Warren, Jiehao Chen, Bin Wu, Qian Wan, Samuel J. Danishefsky

Chemistry

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59 Scopus citations

Abstract

A pathway has been devised, wherein a phenolic ester of a C-terminal peptide is ligated with an N-terminal peptide through two consecutive acyl migrations. In the first transacylation, the C-terminus is transferred from a phenol to a newly liberated ortho-thiol function. Subsequently, the acyl group is transported to a proximal benzylamine through a six-membered transition state.

Original language	English (US)
Pages (from-to)	7460-7462
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	128
Issue number	23
DOIs	https://doi.org/10.1021/ja061588y
State	Published - Jun 14 2006

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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Chen, G., David Warren, J., Chen, J., Wu, B., Wan, Q., & Danishefsky, S. J. (2006). Studies related to the relative thermodynamic stability of C-terminal peptidyl esters of O-hydroxy thiophenol: Emergence of a doable strategy for non-cysteine ligation applicable to the chemical synthesis of glycopeptides. Journal of the American Chemical Society, 128(23), 7460-7462. https://doi.org/10.1021/ja061588y

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abstract = "A pathway has been devised, wherein a phenolic ester of a C-terminal peptide is ligated with an N-terminal peptide through two consecutive acyl migrations. In the first transacylation, the C-terminus is transferred from a phenol to a newly liberated ortho-thiol function. Subsequently, the acyl group is transported to a proximal benzylamine through a six-membered transition state.",

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Chen, G, David Warren, J, Chen, J, Wu, B, Wan, Q & Danishefsky, SJ 2006, 'Studies related to the relative thermodynamic stability of C-terminal peptidyl esters of O-hydroxy thiophenol: Emergence of a doable strategy for non-cysteine ligation applicable to the chemical synthesis of glycopeptides', Journal of the American Chemical Society, vol. 128, no. 23, pp. 7460-7462. https://doi.org/10.1021/ja061588y

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

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T1 - Studies related to the relative thermodynamic stability of C-terminal peptidyl esters of O-hydroxy thiophenol

T2 - Emergence of a doable strategy for non-cysteine ligation applicable to the chemical synthesis of glycopeptides

AU - Chen, Gong

AU - David Warren, J.

AU - Chen, Jiehao

AU - Wu, Bin

AU - Wan, Qian

AU - Danishefsky, Samuel J.

PY - 2006/6/14

Y1 - 2006/6/14

N2 - A pathway has been devised, wherein a phenolic ester of a C-terminal peptide is ligated with an N-terminal peptide through two consecutive acyl migrations. In the first transacylation, the C-terminus is transferred from a phenol to a newly liberated ortho-thiol function. Subsequently, the acyl group is transported to a proximal benzylamine through a six-membered transition state.

AB - A pathway has been devised, wherein a phenolic ester of a C-terminal peptide is ligated with an N-terminal peptide through two consecutive acyl migrations. In the first transacylation, the C-terminus is transferred from a phenol to a newly liberated ortho-thiol function. Subsequently, the acyl group is transported to a proximal benzylamine through a six-membered transition state.

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Chen G, David Warren J, Chen J, Wu B, Wan Q, Danishefsky SJ. Studies related to the relative thermodynamic stability of C-terminal peptidyl esters of O-hydroxy thiophenol: Emergence of a doable strategy for non-cysteine ligation applicable to the chemical synthesis of glycopeptides. Journal of the American Chemical Society. 2006 Jun 14;128(23):7460-7462. doi: 10.1021/ja061588y

Studies related to the relative thermodynamic stability of C-terminal peptidyl esters of O-hydroxy thiophenol: Emergence of a doable strategy for non-cysteine ligation applicable to the chemical synthesis of glycopeptides

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