Simplifying Oligosaccharide Synthesis: Efficient Synthesis of Lactosamine and Siaylated Lactosamine Oligosaccharide Donors | Zendy

Fengyang Yan | Zendy; Seema Mehta | Zendy; Eva Eichler | Zendy; Warren W. Wakarchuk | Zendy; Michel Gilbert | Zendy; M. Schur | Zendy; Dennis M. Whitfield | Zendy

Open Access

Simplifying Oligosaccharide Synthesis: Efficient Synthesis of Lactosamine and Siaylated Lactosamine Oligosaccharide Donors

Author(s) -

Fengyang Yan,

Seema Mehta,

Eva Eichler,

Warren W. Wakarchuk,

Michel Gilbert,

M. Schur,

Dennis M. Whitfield

Publication year - 2003

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo026569v

Subject(s) - oligosaccharide , chemistry , biochemistry

A practical sequence is described for converting d-glucosamine into peracetylated Gal(beta-1,4)GlcNTroc(beta1-S)Ph and Neu5Ac(alpha-2,3)Gal(beta-1,4)GlcNTroc(beta1-S)Ph building blocks using a synthetic strategy based on chemoenzymatic oligosaccharide synthesis. The known trichloroethoxycarbonyl, N-Troc, protecting group was selected as a suitable protecting group for both enzymatic and chemical reaction conditions. These oligosaccharide building blocks proved effective donors for the beta-selective glycosylation of the unreactive OH-3 of a polymeric PEG-bound acceptor and for the axial OH-2 of a mannose acceptor in good yields. The resulting complex oligosaccharides are useful for vaccine and pharmaceutical applications.

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