title: Stereoselective ribosylation of amino acids.
abstract: The glycosylation properties of ribofuranosyl N-phenyltrifluoroacetimidates toward carboxamide side chains of asparagine and glutamine were investigated. Conditions were found that promote nearly exclusive formation of the α-anomerically configured N-glycosides. The strategy allows for the synthesis of Fmoc-amino acids suitably modified for the preparation of ADP-ribosylated peptides. Furthermore, ribosylation of serine with these donors proved to be completely α-selective, and for the first time, α-ribosylated glutamic and aspartic acid, the naturally occurring sites for poly-ADP-ribosylation, were synthesized.
authors.affiliation: Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Hans A V
authors.initials: HA
authors.lastname: Kistemaker
authors.forename: Gerbrand J van der Heden
authors.initials: GJ
authors.lastname: van Noort
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
authors.forename: Dmitri V
authors.initials: DV
authors.lastname: Filippov
mesh_terms: D000246:Adenosine Diphosphate Ribose / Q000031:analogs & derivatives* / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001224:Aspartic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D018698:Glutamic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D012266:Ribose / Q000031:analogs & derivatives* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D000246:Adenosine Diphosphate Ribose; D001224:Aspartic Acid; D018698:Glutamic Acid; D012266:Ribose