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A new Oxyma derivative for nonracemizable amide-forming reactions in water.


ABSTRACT: An Oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (2), displayed remarkable physicochemical properties as a peptide-coupling additive for peptide-forming reactions in water. Short peptides to oligopeptides could be synthesized by using 2, EDCI, and NaHCO(3) in water without measurable racemization. Significantly, a simple basic and acidic aqueous workup procedure can remove all reagents utilized in the reactions to afford only coupling products in consistently excellent yields.

SUBMITTER: Wang Q 

PROVIDER: S-EPMC3431018 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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A new Oxyma derivative for nonracemizable amide-forming reactions in water.

Wang Qinghui Q   Wang Yong Y   Kurosu Michio M  

Organic letters 20120614 13


An Oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (2), displayed remarkable physicochemical properties as a peptide-coupling additive for peptide-forming reactions in water. Short peptides to oligopeptides could be synthesized by using 2, EDCI, and NaHCO(3) in water without measurable racemization. Significantly, a simple basic and acidic aqueous workup procedure can remove all reagents utilized in the reactions to afford only coupling products in consis  ...[more]

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