New Cyclization Reaction at the Amino Terminus of Peptides and Proteins

Article Article scientifique Article New Cyclization Reaction at the Amino Terminus of Peptides and Proteins eng 1999 author Rose Keith 21876 author Chen Jianhua 508255 author Dragovic Marina author Zeng Weiguang 30065 author Jeannerat Damien 45489 author Kamalaprija Philippe 29069 author Burger Ulrich 25497 1038-1043 10.1021/bc9900587 10563773 1043-1802 Mild oxidation with periodate of the 1-amino-2-ol moiety of N-terminal seryl or threonyl peptides and proteins leads to a terminal aldehyde function O=CH-CO- which usually may be exploited for bioconjugate formation (e.g., via oximation with an O-alkyl hydroxylamine). We report that, when followed by a prolyl residue, the O=CH-CO- group can undergo a rapid cyclization and dehydration reaction through nucleophilic attack by the amide nitrogen of the third amino acid residue of the chain. We have characterized the resulting heterocycle, which is stable in aqueous acid, by mass spectrometry and NMR. Quantitative oximation can nevertheless be achieved in such cases by performing a one-pot oxidation-oximation without isolation of the intermediate aldehyde, as is demonstrated with cholera toxin B subunit. Dewey 540 36 Département de chimie organique 141 false Bioconjugate chemistry 10 6 6c225299-710c-4483-9194-afd0421a0108 Article Restricted file1.pdf 85117 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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New Cyclization Reaction at the Amino Terminus of Peptides and Proteins	Bioconjugate chemistry			1999	678	0

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Chen, Jianhua