Document Detail

Synthesis and bioorthogonal coupling chemistry of a novel cyclopentenone-containing unnatural tyrosine analogue.
MedLine Citation:
PMID:  18272199     Owner:  NLM     Status:  MEDLINE    
Herein we report the synthesis of a novel amino acid with orthogonal functionality to the natural amino acid side chains. Tyrosine was O-alkylated with a cyclic 5-membered alpha,beta-unsaturated ketone ring (5). We have established that this amino acid analogue can undergo cycloaddition reactions in aqueous media with in situ generated nitrones. Nitrone formation occurred by micellar catalysis can undergo aqueous 1,3-dipolar cycloaddition reactions with the unnatural Tyr. We also performed a linear free energy analysis of the one pot bioconjugation reaction in water using cyclopentenone as a model for the Tyr analogue and seven different aryl nitrones. We found that the Hammett rho value was -0.94, suggesting that the reaction occurs in a concerted fashion with a slight positive charge buildup in the transition state. The Hammett rho value also suggests that the bioconjugation reaction is tolerant of different substituents and thus may be useful for introducing novel functionality into peptides and proteins containing the Tyr analogue 5. The aqueous 1,3-dipolar cycloaddition reactions, that use nitrones to trap the O-alkylated Tyr 5, establish a novel strategy for rapid, water compatible bioconjugation reactions.
Gianni R Lorello; Marc C B Legault; Bojana Rakić; Kathrine Bisgaard; John Paul Pezacki
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Publication Detail:
Type:  Journal Article     Date:  2008-02-12
Journal Detail:
Title:  Bioorganic chemistry     Volume:  36     ISSN:  1090-2120     ISO Abbreviation:  Bioorg. Chem.     Publication Date:  2008 Apr 
Date Detail:
Created Date:  2008-03-10     Completed Date:  2008-07-24     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  1303703     Medline TA:  Bioorg Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  105-11     Citation Subset:  IM    
Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ont., Canada.
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MeSH Terms
Chemistry, Organic / methods
Cyclopentanes / chemistry*
Tyrosine / analogs & derivatives*
Reg. No./Substance:
0/Cyclopentanes; 55520-40-6/Tyrosine; 930-30-3/cyclopentenone

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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