Activation of d-Asparagine and d-Glutamine Derivatives Using the Mitsunobu Reaction

Xuan Fu; Yuqin Shang; Shengxi Chen; Larisa M. Dedkova; Sidney M. Hecht

doi:10.1021/acs.orglett.3c00232

Activation of d-Asparagine and d-Glutamine Derivatives Using the Mitsunobu Reaction

Xuan Fu, Yuqin Shang, Shengxi Chen, Larisa M. Dedkova, Sidney M. Hecht

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

Abstract

Seven d-amino acid derivatives having reactive side chains have been activated to afford their respective 3,5-dinitrobenzyl esters using the Mitsunobu reaction. This esterification was found to be difficult using traditional methods involving 3,5-dinitrobenzyl chloride under alkaline conditions. The conversion of a tRNA to the respective d-glutaminyl-tRNA using d-glutamine 3,5-dinitrobenzyl ester was catalyzed by a flexizyme, followed by purification to remove all the unacylated tRNAs and other byproducts. Both d- and l-glutamine were incorporated from their aminoacyl-tRNAs into a model peptide structurally related to IFN-β.

Original language	English (US)
Pages (from-to)	1310-1314
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.3c00232
State	Published - Mar 3 2023

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.3c00232

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title = "Activation of d-Asparagine and d-Glutamine Derivatives Using the Mitsunobu Reaction",

abstract = "Seven d-amino acid derivatives having reactive side chains have been activated to afford their respective 3,5-dinitrobenzyl esters using the Mitsunobu reaction. This esterification was found to be difficult using traditional methods involving 3,5-dinitrobenzyl chloride under alkaline conditions. The conversion of a tRNA to the respective d-glutaminyl-tRNA using d-glutamine 3,5-dinitrobenzyl ester was catalyzed by a flexizyme, followed by purification to remove all the unacylated tRNAs and other byproducts. Both d- and l-glutamine were incorporated from their aminoacyl-tRNAs into a model peptide structurally related to IFN-β.",

author = "Xuan Fu and Yuqin Shang and Shengxi Chen and Dedkova, {Larisa M.} and Hecht, {Sidney M.}",

note = "Funding Information: This work was supported by a research grant from Ionis Pharmaceuticals. Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

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doi = "10.1021/acs.orglett.3c00232",

language = "English (US)",

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T1 - Activation of d-Asparagine and d-Glutamine Derivatives Using the Mitsunobu Reaction

AU - Fu, Xuan

AU - Shang, Yuqin

AU - Chen, Shengxi

AU - Dedkova, Larisa M.

AU - Hecht, Sidney M.

PY - 2023/3/3

Y1 - 2023/3/3

N2 - Seven d-amino acid derivatives having reactive side chains have been activated to afford their respective 3,5-dinitrobenzyl esters using the Mitsunobu reaction. This esterification was found to be difficult using traditional methods involving 3,5-dinitrobenzyl chloride under alkaline conditions. The conversion of a tRNA to the respective d-glutaminyl-tRNA using d-glutamine 3,5-dinitrobenzyl ester was catalyzed by a flexizyme, followed by purification to remove all the unacylated tRNAs and other byproducts. Both d- and l-glutamine were incorporated from their aminoacyl-tRNAs into a model peptide structurally related to IFN-β.

AB - Seven d-amino acid derivatives having reactive side chains have been activated to afford their respective 3,5-dinitrobenzyl esters using the Mitsunobu reaction. This esterification was found to be difficult using traditional methods involving 3,5-dinitrobenzyl chloride under alkaline conditions. The conversion of a tRNA to the respective d-glutaminyl-tRNA using d-glutamine 3,5-dinitrobenzyl ester was catalyzed by a flexizyme, followed by purification to remove all the unacylated tRNAs and other byproducts. Both d- and l-glutamine were incorporated from their aminoacyl-tRNAs into a model peptide structurally related to IFN-β.

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Activation of d-Asparagine and d-Glutamine Derivatives Using the Mitsunobu Reaction

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