Syntheses of sugar poly(orthoesters) through reverse anomeric effect

Lingyao Li; Jun Wang; Melissa Obrinske; Ian Milligan; Kylie O'Hara; Lindsay Bitterman; Wenjun Du

doi:10.1039/c5cc00332f

Syntheses of sugar poly(orthoesters) through reverse anomeric effect

Chem Commun (Camb). 2015 Apr 25;51(32):6972-5. doi: 10.1039/c5cc00332f. Epub 2015 Mar 23.

Authors

Lingyao Li¹, Jun Wang, Melissa Obrinske, Ian Milligan, Kylie O'Hara, Lindsay Bitterman, Wenjun Du

Affiliation

¹ Department of Chemistry and Biochemistry, Science of Advanced Materials, Central Michigan University, Mount Pleasant, MI 48859, USA. [email protected].

PMID: 25797911
DOI: 10.1039/c5cc00332f

Abstract

High molecular weight sugar poly(orthoesters) were synthesized through reverse anomeric effect (RAE). We demonstrated that when RAE-enabled promoters, such as 4-(dimethylamino)pyridine (DMAP), triphenylphosphine (TPP) or imidazole, were employed, efficient polymerizations were achieved, giving sugar poly(orthoesters) with molecular weights up to 18 kDa.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Carbohydrates / chemistry*
Chemistry Techniques, Synthetic
Polyesters / chemical synthesis*
Polyesters / chemistry*
Stereoisomerism

Substances

Carbohydrates
Polyesters