Silyl protection in the solid-phase synthesis of N-linked glycopeptides. Preparation of glycosylated fluorogenic substrates for subtilisins

I Christiansen-Brams; A M Jansson; M Meldal; K Breddam; K Bock

doi:10.1016/s0968-0896(00)82067-2

Silyl protection in the solid-phase synthesis of N-linked glycopeptides. Preparation of glycosylated fluorogenic substrates for subtilisins

Bioorg Med Chem. 1994 Nov;2(11):1153-67. doi: 10.1016/s0968-0896(00)82067-2.

Authors

I Christiansen-Brams¹, A M Jansson, M Meldal, K Breddam, K Bock

Affiliation

¹ Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark.

PMID: 7757413
DOI: 10.1016/s0968-0896(00)82067-2

Abstract

The trimethylsilyl (TMS) group was used for protection of the hydroxy groups of three disaccharide 1-amino-alditols and of the glycosylamines of glucose, maltotriose and maltoheptose. The per-O-trimethylsilylated derivatives were coupled with N alpha-Fmoc-Asp(Cl)-OPfp 7 to give six glycosylated building blocks for the solid-phase synthesis of N-linked glycopeptides. Building block 8 was used in the synthesis of five internally quenched fluorescent substrates which were studied by enzymatic hydrolysis with savinase, a subtilisin-type enzyme.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acid Sequence
Binding Sites
Carbohydrate Metabolism
Carbohydrate Sequence
Computer Graphics
Fluorescence
Fluorine Compounds / chemical synthesis
Glycopeptides / chemical synthesis*
Glycopeptides / metabolism
Magnetic Resonance Spectroscopy
Molecular Sequence Data
Molecular Structure
Serine Endopeptidases / metabolism
Subtilisins / metabolism*
Sugar Alcohols / chemistry
Trimethylsilyl Compounds / chemistry*

Substances

Fluorine Compounds
Glycopeptides
Sugar Alcohols
Trimethylsilyl Compounds
Serine Endopeptidases
Subtilisins
microbial serine proteinases
lactitol