Chemoselective Staudinger-phosphite reaction of symmetrical glycosyl-phosphites with azido-peptides and polygycerols.
In this paper we present the synthesis of glyco-phosphoramidate conjugates as easily accessible analogs of glyco-phosphorous esters via the Staudinger-phosphite reaction. This protocol takes advantage of synthetically accessible symmetrical carbohydrate phosphites in good overall yields, in which ethylene or propylene linkers can be introduced between phosphorous and galactose or lactose moieties. The phosphites were finally applied for the chemoselective reaction with azido-peptides and polyazido(poly)glycerols.
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany.
Verena
V
Böhrsch
Thresen
T
Mathew
Maximilian
M
Zieringer
M Robert J
MR
Vallée
Lukas M
LM
Artner
Jens
J
Dernedde
Rainer
R
Haag
Christian P R
CP
Hackenberger
D001386:Azides / Q000737:chemistry*; D003712:Dendrites / Q000737:chemistry; D005990:Glycerol / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D017905:Phosphites / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D001386:Azides; D006020:Glycopeptides; D017905:Phosphites; D005990:Glycerol