Synthesis of the tetrasaccharide repeating unit of the cryoprotectant capsular polysaccharide from Colwellia psychrerythraea 34H

文献情報

出版日 2019-02-27

DOI 10.1039/C9OB00104B

インパクトファクター 3.876

著者

Giulia Vessella, Angela Casillo, Antonio Fabozzi, Serena Traboni, Alfonso Iadonisi, Maria Michela Corsaro, Emiliano Bedini

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要旨

Colwellia psychrerythraea 34H is a psychrophilic Gram-negative bacterium, able to survive at subzero temperatures by producing a unique capsular polysaccharide (CPS) with anti-freeze properties similar to those of the well-known anti-freeze (glyco)proteins. The tetrasaccharide repeating unit of the CPS – constituted of alternating amino sugars and uronic acid moieties in a glycosaminoglycan-like fashion with an amide-linked threonine (Thr) decoration – was synthesized as an O-n-propyl glycoside. The synthesis faced some challenging features such as building up a crowded [→2)α-D-Galp(1→] moiety as well as differentiating the two uronic units for the regioselective insertion of the Thr amide only on one of them. NMR data for the obtained tetrasaccharide confirmed the structure proposed for the C. psychrerythraea polysaccharide.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Synthesis of the tetrasaccharide repeating unit of the cryoprotectant capsular polysaccharide from Colwellia psychrerythraea 34H

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Organic & Biomolecular Chemistry

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