Solid-Phase Synthesis of Thioether-Linked Glycopeptide Mimics for Application to Glycoprotein Semisynthesis

Glycoproteins are particularly suited to protein semisynthesis since homogeneous samples for biological analyses are not readily available using traditional recombinant techniques. Here we apply glycosyl iodoacetamides, normally used for the modification of bacterially derived proteins, to solid-pha...

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Bibliographic Details
Published inOrganic letters Vol. 4; no. 9; pp. 1467 - 1470
Main Authors Macmillan, Derek, Daines, Alison M, Bayrhuber, Monika, Flitsch, Sabine L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.05.2002
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Chromatography, High Pressure Liquid
Cysteine - chemistry
Glycopeptides - chemistry
Glycoproteins - chemical synthesis
Indicators and Reagents
Models, Chemical
Molecular Mimicry
Physical Sciences
Science & Technology
Spectrometry, Mass, Electrospray Ionization
Sulfhydryl Compounds - chemistry
ANALOG
ROLES
CARBOHYDRATE
CHEMICAL-SYNTHESIS
GLYCOSYLATION
PROTEINS
GLYCAN
DIRECTIONS
ANTIGEN
VACCINES
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Summary:Glycoproteins are particularly suited to protein semisynthesis since homogeneous samples for biological analyses are not readily available using traditional recombinant techniques. Here we apply glycosyl iodoacetamides, normally used for the modification of bacterially derived proteins, to solid-phase glycopeptide synthesis. This provides access to glycopeptide α-thioesters, which may lend themselves to the semisynthesis of homogeneous N-linked glycoprotein mimics and novel glycopeptide libraries.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol025627w