Journal article
Synthesis, separation, and characterization of amphiphilic sulfated oligosaccharides enabled by reversed-phase ion pairing LC and LC-MS methods
Carbohydrate research, Vol.346(17), pp.2792-2800
12/13/2011
DOI: 10.1016/j.carres.2011.09.020
PMCID: PMC3221801
PMID: 22015170
Abstract
Synthesis of amphiphilic oligosaccharides is problematic because traditional methods for separating and purifying oligosaccharides, including sulfated oligosaccharides, are generally not applicable to working with amphiphilic sugars. We report here RPIP-LC and LC-MS methods that enable the synthesis, separation, and characterization of amphiphilic N-arylacyl O-sulfonated aminoglycosides, which are being pursued as small-molecule glycosaminoglycan mimics. The methods described in this work for separating and characterizing these amphiphilic saccharides are further applied to a number of uses: monitoring the progression of sulfonation reactions with analytical RP-HPLC, characterizing sulfate content for individual molecules with ESI-MS, determining the degree of sulfation for products having mixed degrees of sulfation with HPLC and LC-MS, and purifying products with benchtop C18 column chromatography. We believe that the methods described here will be broadly applicable to enabling the synthesis, separation, and characterization of amphiphilic, sulfated, and phosphorylated oligosaccharides and other types of molecules substituted to varying degrees with both anionic and hydrophobic groups. (C) 2011 Elsevier Ltd. All rights reserved.
Details
- Title: Subtitle
- Synthesis, separation, and characterization of amphiphilic sulfated oligosaccharides enabled by reversed-phase ion pairing LC and LC-MS methods
- Creators
- Amanda M. Fenner - University of IowaRobert J. Kerns - Univ Iowa, Div Med & Nat Prod Chem, Iowa City, IA 52242 USA
- Resource Type
- Journal article
- Publication Details
- Carbohydrate research, Vol.346(17), pp.2792-2800
- Publisher
- Elsevier
- DOI
- 10.1016/j.carres.2011.09.020
- PMID
- 22015170
- PMCID
- PMC3221801
- ISSN
- 0008-6215
- eISSN
- 1873-426X
- Number of pages
- 9
- Grant note
- T32GM067795 / NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Institute of General Medical Sciences (NIGMS) American Foundation for Pharmaceutical Education T32 GM067795 / NIH; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA Bristol-Myers Squibb ACS Division of Medicinal Chemistry
- Language
- English
- Date published
- 12/13/2011
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
- Record Identifier
- 9984365892402771
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