Racemization of an asparagine residue during peptide deamidation.

Racemization of an asparagine residue during peptide deamidation. Research Abstract Details 

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Racemization of an asparagine residue during peptide deamidation. Abstract Text:

Bei Li,Ronald T Borchardt,Elizabeth M Topp,David VanderVelde,Richard L Schowen,

The Asn residue in the pentapeptide Asn-Gln-Asn-Glu-Gly undergoes racemization at the Calpha center in the course of deamidation of this residue through a succinimide intermediate. The succinimide intermediate is known to racemize at the corresponding center, leading to racemized products of deamidation. Return of this intermediate to reactant Asn is very unlikely in dilute solution where attack of product ammonia on the succinimide is precluded, and Asn racemization has not been previously observed. We give evidence that the observed racemization occurs at the tetrahedral-intermediate stage preceding the succinimide intermediate. The observation is significant for protein stability in vivo and in vitro and has importance in medicine, food chemistry, and archaeological/palaeological dating.

Racemization of an asparagine residue during peptide deamidation. Publishing Authors By Initials

B Li,RT Borchardt,EM Topp,D VanderVelde,RL Schowen,

For similar organic chemicals: imides: succinimides research abstracts see: organic chemicals: imides: succinimides research

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Racemization of an asparagine residue during peptide deamidation. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 125

Page Numbers: 11486-7

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 24

MONTH: Sep

YEAR: 2003

Racemization of an asparagine residue during peptide deamidation. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 7503056

Racemization of an asparagine residue during peptide deamidation. Keywords Mesh Terms:

KEYWORDS: Succinimides

MESH TERMS: chemistry

Chemical & Substance for Abstract: Racemization of an asparagine residue during peptide deamidation. Information

Substance Name: Asparagine

Registry Number: 7006-34-0

Grant and Affiliation Information for Racemization of an asparagine residue during peptide deamidation.

AFFILIATION: Department of Pharmaceutical Chemistry, The University of Kansas, 2095 Constant Avenue, Lawrence, Kansas 66047, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: GM54195

ACRONYM: GM

MEDLINETA: J Am Chem Soc

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