Chemical synthesis of the 4-amino-4,6-dideoxy-d-glucose containing pentasaccharide repeating unit of the O-specific polysaccharide from Aeromonas hydrophila strain K691 in the form of its 2-aminoethyl glycoside

Anirban Adak; Balaram Mukhopadhyay

doi:10.1016/j.carres.2019.02.009

Chemical synthesis of the 4-amino-4,6-dideoxy-d-glucose containing pentasaccharide repeating unit of the O-specific polysaccharide from Aeromonas hydrophila strain K691 in the form of its 2-aminoethyl glycoside

Carbohydr Res. 2019 Apr 1:476:1-7. doi: 10.1016/j.carres.2019.02.009. Epub 2019 Mar 5.

Authors

Anirban Adak¹, Balaram Mukhopadhyay²

Affiliations

¹ Sweet Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Kolkata, Mohanpur, Nadia, 741246, India.
² Sweet Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Kolkata, Mohanpur, Nadia, 741246, India. Electronic address: mbalaram@iiserkol.ac.in.

PMID: 30861377
DOI: 10.1016/j.carres.2019.02.009

Abstract

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Aeromonas hydrophilastrain K691 is reported. Synthesis of the pentasaccharide is accomplished by using a common disaccharide in sequence and finally attaching the rare sugar unit. The target structure was made in the form of its 2-aminoethyl glycoside which is essential for further glycconjugate formation. Stereoselective glycosylations were achieved by the activation of thioglycosides in the presence of H₂SO₄-silica in conjunction with N-iodosuccinimide.

Keywords: 4-Amino-4,6-dideoxy-d-glucose; Fish pathogen; H(2)SO(4)-Silica; O-specific polysaccharide; Total synthesis.

MeSH terms

Aeromonas hydrophila / chemistry*
Chemistry Techniques, Synthetic
Glucosamine / analogs & derivatives*
Glucosamine / chemistry
Glycosides / chemistry*
O Antigens / chemistry*

Substances

4-amino-4,6-dideoxyglucose
Glycosides
O Antigens
Glucosamine