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Investigation of the Amide Proton Solvent Exchange Properties of Glycosaminoglycan Oligosaccharides
Green, Andrew R.1; Li, Kecheng1,2,3; Lockard, Blake1; Young, Robert P.1,4; Mueller, Leonard J.1; Larive, Cynthia K.1
2019-06-06
Source PublicationJOURNAL OF PHYSICAL CHEMISTRY B
ISSN1520-6106
Volume123Issue:22Pages:4653-4662
Corresponding AuthorLarive, Cynthia K.(clarive@ucr.edu)
AbstractOne-dimensional H-1 NMR experiments were conducted for aqueous solutions of glycosaminoglycan oligosaccharides to measure the amide proton temperature coefficients and activation energy barriers for solvent exchange and evaluate the effect of pH on the solvent exchange properties. A library of mono- and oligosaccharides was prepared by enzymatic depolymerization of amide-containing polysaccharides and by chemical modification of heparin and heparan sulfate saccharides including members that contain a 3-O-sulfated glucosamine residue. The systematic evaluation of this saccharide library facilitated assessment of the effects of structural characteristics, such as size, sulfation number and site, and glycosidic linkage, on amide proton solvent exchange rates. Charge repulsion by neighboring negatively charged sulfate and carboxylate groups was found to have a significant impact on the catalysis of amide proton solvent exchange by hydroxide. This observation leads to the conclusion that solvent exchange rates must be interpreted within the context of a given chemical environment. On their own, slow exchange rates do not conclusively establish the involvement of a labile proton in a hydrogen bond, and additional supporting experimental evidence such as reduced temperature coefficients is required.
DOI10.1021/acs.jpcb.9b01794
Indexed BySCI
Language英语
Funding ProjectNSF[CHE-1626673] ; NIH[R01GM097569] ; China Scholarship Council[201504910405]
WOS Research AreaChemistry
WOS SubjectChemistry, Physical
WOS IDWOS:000470938100005
PublisherAMER CHEMICAL SOC
Citation statistics
Document Type期刊论文
Identifierhttp://ir.qdio.ac.cn/handle/337002/161835
Collection实验海洋生物学重点实验室
Corresponding AuthorLarive, Cynthia K.
Affiliation1.Univ Calif Riverside, Dept Chem, Riverside, CA 92501 USA
2.Chinese Acad Sci, Inst Oceanol, Ctr Ocean Megasci, Key Lab Expt Marine Biol, Qingdao 266071, Shandong, Peoples R China
3.Qingdao Natl Lab Marine Sci & Technol, Lab Marine Drugs & Bioprod, Qingdao 266237, Shandong, Peoples R China
4.Pacific Northwest Natl Lab, Environm Mol Sci Lab, Richland, WA 99352 USA
Recommended Citation
GB/T 7714
Green, Andrew R.,Li, Kecheng,Lockard, Blake,et al. Investigation of the Amide Proton Solvent Exchange Properties of Glycosaminoglycan Oligosaccharides[J]. JOURNAL OF PHYSICAL CHEMISTRY B,2019,123(22):4653-4662.
APA Green, Andrew R.,Li, Kecheng,Lockard, Blake,Young, Robert P.,Mueller, Leonard J.,&Larive, Cynthia K..(2019).Investigation of the Amide Proton Solvent Exchange Properties of Glycosaminoglycan Oligosaccharides.JOURNAL OF PHYSICAL CHEMISTRY B,123(22),4653-4662.
MLA Green, Andrew R.,et al."Investigation of the Amide Proton Solvent Exchange Properties of Glycosaminoglycan Oligosaccharides".JOURNAL OF PHYSICAL CHEMISTRY B 123.22(2019):4653-4662.
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