Synthetic 6-O-Methylglucose-Containing Polysaccharides (sMGPs):  Design and Synthesis

• Published in: Journal of organic chemistry Vol. 72; no. 6; pp. 1941 - 1950
• Main Authors: Meppen, Malte, Wang, Yonghui, Cheon, Hwan-Sung, Kishi, Yoshito
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.03.2007; Amer Chemical Soc
• Subjects: Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Organic; Cyclodextrins - chemistry; Drug Design; Exact sciences and technology; Glycosylation; Methylglucosides - chemistry; Molecular Mimicry; Oligosaccharides - chemical synthesis; Organic chemistry; Physical Sciences; Polysaccharides - chemical synthesis; Preparations and properties; Science & Technology; SILVER PERCHLORATE; ALPHA-CYCLODEXTRIN; PHLEI; REVISED STRUCTURE; METHYL GLUCOSE POLYSACCHARIDES; BIOSYNTHESIS; LIPOPOLYSACCHARIDE; BETA-CYCLODEXTRINS; DERIVATIVES; MYCOBACTERIAL METHYLMANNOSE POLYSACCHARIDE; Biological properties; Molecular flexibility; Aldose; Oside; Glycosylation; Mannose; Selectivity; Glucose; Oligomer; Cyclodextrin; Glycoside; Inclusion compound; Chemical synthesis; Polysaccharide
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo061990v

With the hope of mimicking the chemical and biological properties of natural 6-O-methyl-d-glucose-containing polysaccharides (MGPs), synthetic 6-O-methyl-d-glucose-containing polysaccharides (sMGPs) were designed and synthesized from α-, β-, and γ-cyclodextrins (CDs). The synthetic route proved to be flexible and general, to furnish a series of sMGPs ranging from 6-mer to 20-mer. A practical and scalable method was discovered selectively to cleave the CD derivatives and furnish the linear precursors to the glycosyl donors and acceptors. The Mukaiyama glycosidation was adopted to couple the glycosyl donors with the glycosyl acceptors. Unlike in the 3-O-methyl-d-mannose-containing polysaccharide (sMMP) series, the amount of the Mukaiyama acid required in the sMGP series increased with an increase of substrate size; that is, for large oligomers, more than one equivalent of the acid was required.