Investigations into the role of oxacarbenium ions in glycosylation reactions by ab initio molecular dynamics

Download
  1. Get@NRC: Investigations into the role of oxacarbenium ions in glycosylation reactions by ab initio molecular dynamics (Opens in a new window)
DOIResolve DOI: http://doi.org/10.1016/j.carres.2006.09.027
AuthorSearch for: ; Search for: ; Search for: ; Search for:
TypeArticle
Journal titleCarbohydrate Research
Volume341
Issue18
Pages29122920; # of pages: 9
SubjectConformations; Glycosylation; Oxacarbenium ions; role; glycosylation; molecular; molecular dynamics; molecular-dynamics; dynamics
AbstractWe present a constrained ab initio molecular dynamics method that allows the modeling of the conformational interconversions of glycopyranosyl oxacarbenium ions. The model was successfully tested by estimating the barriers to ring inversion for two 4-substituted tetrahydropyranosyl oxacarbenium ions. The model was further extended to predict the pathways that connect the 4H3 half-chair conformation of 2,3,4,6-tetra-O-methyl-d-glucopyranosyl cation to its inverted 5S1 conformation and the 4H3 half-chair conformation of 2,3,4,6-tetra-O-methyl-d-mannopyranosyl cation to its inverted 3E conformation. The modeled interconversion pathways reconcile a large body of experimental work on the acid-catalyzed hydrolysis of glycosides and the mechanisms of a number of glucosidases and mannosidases.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; NRC Institute for Biological Sciences; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
NRC numberIONESCU2006
NPARC number12335893
Export citationExport as RIS
Report a correctionReport a correction
Record identifier4c79fe6c-0ec7-46af-bf92-a7429b1c251b
Record created2009-09-10
Record modified2016-05-09
Bookmark and share
  • Share this page with Facebook (Opens in a new window)
  • Share this page with Twitter (Opens in a new window)
  • Share this page with Google+ (Opens in a new window)
  • Share this page with Delicious (Opens in a new window)