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DOI: 10.1055/s-2008-1032150
Efficient Synthesis of Glycosylated Asparaginic Acid Building Blocks via Click Chemistry
Publication History
Publication Date:
31 January 2008 (online)
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Abstract
A series of per-O-acetyl-glycose-Fmoc-l-Asp(O-t-Bu) derivatives and tert-butyl per-O-acetyl-glycose-(S)-3-fluorenylmethyloxycarbamidobutyrates were prepared by copper-catalyzed 1,3-dipolar cycloaddition of fully acetylated propargyl 1-thioglycosides (gluco, galacto, manno and rhamno series) and Fmoc-l-Asp(O-t-Bu)propargyl amide with tert-butyl (S)-4-azido-3-fluorenylmethyloxycarbamidobutyrate, 2,3,4,6-tri-O-acetyl-glycosyl azides and ethyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-1-thioglycosides (gluco, galacto, manno series), respectively (click chemistry). Thus obtained orthogonally protected l-asparaginic and (S)-3-aminobutyric acids bearing an acetyl-protected glycose or glycoside moiety, linked through a triazole spacer, are suitable building blocks for combinatorial glycopeptide syntheses.
Key words
amino acids - azides - carbohydrates - 1,3-dipolar cycloadditions - glycosides - glycopeptides - heterocycles
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