Synthetic 6-O-methylglucose-containing polysaccharides (sMGPs): design and synthesis.
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 alpha-, beta-, and gamma-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.
Meppen
Malte
M
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Wang
Yonghui
Y
Cheon
Hwan-Sung
HS
Kishi
Yoshito
Y
D003505:Cyclodextrins / Q000737:chemistry; D015195:Drug Design; D006031:Glycosylation; D008757:Methylglucosides / Q000737:chemistry*; D018716:Molecular Mimicry; D009844:Oligosaccharides / Q000138:chemical synthesis; D011134:Polysaccharides / Q000138:chemical synthesis*
D003505:Cyclodextrins; D008757:Methylglucosides; D009844:Oligosaccharides; D011134:Polysaccharides; C033884:6-O-methylglucose