Effect of residual water and microwave heating on half-lifes of reagents and reactive intermediates in peptide synthesis

Anne Pernille Tofteng Shelton; Søren Ljungberg Pedersen; Dan Stærk; Knud Jørgen Jensen

doi:10.1002/chem.201200711

Effect of residual water and microwave heating on half-lifes of reagents and reactive intermediates in peptide synthesis

Anne Pernille Tofteng Shelton, Søren Ljungberg Pedersen, Dan Stærk, Knud Jørgen Jensen

Kemisk Institut

17 Citationer (Scopus)

Abstract

Precise microwave heating has changed the way many small molecules are being synthesized and, currently, the field of solid-phase peptide synthesis is undergoing dramatic changes owing to the use of microwave heating. To fully reap the benefits of precise microwave heating for the formation of amide bonds in peptide synthesis, it is important to understand the kinetics of formation and break-down of activated esters and their N-acylation of the nascent peptide chain at elevated temperatures. Herein, we present systematic studies of, first, the rate of formation of activated esters by NMR spectroscopy and, second, their N-acylation during peptide synthesis. A study of the amount of residual water in the solvents revealed a significant effect on electrophilic reagents and intermediates. This observation was expanded into a general study of microwave heating in peptide synthesis.

Originalsprog	Engelsk
Tidsskrift	Chemistry: A European Journal
Vol/bind	18
Udgave nummer	29
Sider (fra-til)	9024-9031
Antal sider	8
ISSN	0947-6539
DOI	https://doi.org/10.1002/chem.201200711
Status	Udgivet - 16 jul. 2012

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10.1002/chem.201200711

Citationsformater

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AU - Shelton, Anne Pernille Tofteng

AU - Pedersen, Søren Ljungberg

AU - Stærk, Dan

AU - Jensen, Knud Jørgen

PY - 2012/7/16

Y1 - 2012/7/16

N2 - Precise microwave heating has changed the way many small molecules are being synthesized and, currently, the field of solid-phase peptide synthesis is undergoing dramatic changes owing to the use of microwave heating. To fully reap the benefits of precise microwave heating for the formation of amide bonds in peptide synthesis, it is important to understand the kinetics of formation and break-down of activated esters and their N-acylation of the nascent peptide chain at elevated temperatures. Herein, we present systematic studies of, first, the rate of formation of activated esters by NMR spectroscopy and, second, their N-acylation during peptide synthesis. A study of the amount of residual water in the solvents revealed a significant effect on electrophilic reagents and intermediates. This observation was expanded into a general study of microwave heating in peptide synthesis.

AB - Precise microwave heating has changed the way many small molecules are being synthesized and, currently, the field of solid-phase peptide synthesis is undergoing dramatic changes owing to the use of microwave heating. To fully reap the benefits of precise microwave heating for the formation of amide bonds in peptide synthesis, it is important to understand the kinetics of formation and break-down of activated esters and their N-acylation of the nascent peptide chain at elevated temperatures. Herein, we present systematic studies of, first, the rate of formation of activated esters by NMR spectroscopy and, second, their N-acylation during peptide synthesis. A study of the amount of residual water in the solvents revealed a significant effect on electrophilic reagents and intermediates. This observation was expanded into a general study of microwave heating in peptide synthesis.

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DO - 10.1002/chem.201200711

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JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

IS - 29

ER -

Effect of residual water and microwave heating on half-lifes of reagents and reactive intermediates in peptide synthesis

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