Water-driven chemoselective reaction of squarate derivatives with amino acids and peptides

Preeti Sejwal; Yongbin Han; Akshay Shah; Yan Yeung Luk

doi:10.1021/ol702275q

Water-driven chemoselective reaction of squarate derivatives with amino acids and peptides

Preeti Sejwal, Yongbin Han, Akshay Shah, Yan Yeung Luk

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

29 Scopus citations

Abstract

(Chemical Equation Presented) Here, we report a new class of highly chemoselective reactions between squarate derivatives and the amino acid cysteine or unprotected peptides with a N-terminus cysteine that proceed most efficiently in entirely aqueous solution at neutral pH. Kinetic and structural studies reveal that the presence of hydrogen bonding in water is primarily responsible for both the high yield and fast rate of the reaction.

Original language	English (US)
Pages (from-to)	4897-4900
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	23
DOIs	https://doi.org/10.1021/ol702275q
State	Published - Nov 8 2007

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol702275q

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title = "Water-driven chemoselective reaction of squarate derivatives with amino acids and peptides",

abstract = "(Chemical Equation Presented) Here, we report a new class of highly chemoselective reactions between squarate derivatives and the amino acid cysteine or unprotected peptides with a N-terminus cysteine that proceed most efficiently in entirely aqueous solution at neutral pH. Kinetic and structural studies reveal that the presence of hydrogen bonding in water is primarily responsible for both the high yield and fast rate of the reaction.",

author = "Preeti Sejwal and Yongbin Han and Akshay Shah and Luk, {Yan Yeung}",

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AU - Sejwal, Preeti

AU - Han, Yongbin

AU - Shah, Akshay

AU - Luk, Yan Yeung

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Y1 - 2007/11/8

N2 - (Chemical Equation Presented) Here, we report a new class of highly chemoselective reactions between squarate derivatives and the amino acid cysteine or unprotected peptides with a N-terminus cysteine that proceed most efficiently in entirely aqueous solution at neutral pH. Kinetic and structural studies reveal that the presence of hydrogen bonding in water is primarily responsible for both the high yield and fast rate of the reaction.

AB - (Chemical Equation Presented) Here, we report a new class of highly chemoselective reactions between squarate derivatives and the amino acid cysteine or unprotected peptides with a N-terminus cysteine that proceed most efficiently in entirely aqueous solution at neutral pH. Kinetic and structural studies reveal that the presence of hydrogen bonding in water is primarily responsible for both the high yield and fast rate of the reaction.

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Water-driven chemoselective reaction of squarate derivatives with amino acids and peptides

Abstract

ASJC Scopus subject areas

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