title: Chemical synthesis of asparagine-linked archaeal N-glycan from Methanothermus fervidus.
abstract: Several N-linked glycoproteins have been identified in archaea and there is growing evidence that the N-glycan is involved in survival and functioning of archaea in extreme conditions. Chemical synthesis of the archaeal N-glycans represents a crucial step towards understanding the putative function of protein glycosylation in archaea. Herein the first total synthesis of the archaeal L-asparagine linked hexasaccharide from Methanothermus fervidus is reported using a highly convergent [3+3] glycosylation approach in high overall yields. The synthesis relies on efficient preparation of regioselectively protected thioglycoside building blocks for orthogonal glycosylations and late stage N-aspartylation.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076 (India).
authors.forename: Someswara Rao
authors.initials: SR
authors.lastname: Sanapala
authors.forename: Suvarn S
authors.initials: SS
authors.lastname: Kulkarni
mesh_terms: D001105:Archaea / Q000737:chemistry*; D001216:Asparagine / Q000138:chemical synthesis* / Q000737:chemistry; D006023:Glycoproteins / Q000378:metabolism; D006031:Glycosylation; D015394:Molecular Structure; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006023:Glycoproteins; D011134:Polysaccharides; D001216:Asparagine
keywords: N-aspartylation; N-glycans; archaea; glycoproteins; glycosylation