A1 Refereed original research article in a scientific journal
Tagging of phosphopeptides by phosphate elimination and Michael addition: The effect of nearest neighbors on the reaction kinetics
Authors: Mattila K, Ora M, Lonnberg H
Publisher: BENTHAM SCIENCE PUBL LTD
Publication year: 2006
Journal:: Letters in Organic Chemistry
Journal name in source: LETTERS IN ORGANIC CHEMISTRY
Journal acronym: LETT ORG CHEM
Volume: 3
Issue: 7
First page : 514
Last page: 518
Number of pages: 5
ISSN: 1570-1786
DOI: https://doi.org/10.2174/157017806778341924
Abstract
Kinetics of the base-catalyzed elimination of the phosphate group from short phosphoserinyl peptides and subsequent addition of beta-mercaptoethanol to the dehydroalaninyl residue have been studied by following the reactions by RP HPLC in an 8:3:1 (vlvlv) mixture of water, DMSO and ethanol. The data obtained shows that neighboring side-chain-functionalized residues, including Asp, Tyr, Lys, His, Pro and Asn, influence the rate of elimination and addition steps by less than one order of magnitude. The amount of byproducts always remains below 10 %, lending support to the applicability of the method as a research tool for functional phosphoproteornics.
Kinetics of the base-catalyzed elimination of the phosphate group from short phosphoserinyl peptides and subsequent addition of beta-mercaptoethanol to the dehydroalaninyl residue have been studied by following the reactions by RP HPLC in an 8:3:1 (vlvlv) mixture of water, DMSO and ethanol. The data obtained shows that neighboring side-chain-functionalized residues, including Asp, Tyr, Lys, His, Pro and Asn, influence the rate of elimination and addition steps by less than one order of magnitude. The amount of byproducts always remains below 10 %, lending support to the applicability of the method as a research tool for functional phosphoproteornics.
UTU Research Portal