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Chemical Synthesis of Glycopeptides

  • Christian Haase
  • Oliver Seitz
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 267)

Abstract

Despite its omnipresence in nature, comparatively little is known about how glycosylation affects the function and activity of proteins. To understand the role of protein glycosylation at the molecular level, it is important to have access to homogeneous glycoproteins and glycopeptides. Chemical synthesis is particularly suited to provide uniform glycoprotein material, thus playing a pivotal role for the advancement of glycobiology. This chapter summarizes the recent progress achieved in glycopeptide synthesis including new glycosylation methods, enzymatic transformations, chemoselective ligation and recombinant expression.

Glycobiology Glycopeptides Chemoenzymatic Solid-phase synthesis Chemoselective ligation 

Abbreviations

Ac

Acetyl

Acm

Acetamidomethyl

Aloc

Allyloxycarbonyl

Bn, Bzl

Benzyl

Boc

tert-Butyloxycarbonyl

Bu

Butyl

BSA

Bovine serum albumin

CLEAR

Cross-linked ethoxylate acrylate resin

CMP

Cytidine monophosphate

DCC

Dicyclohexylcarbodiimide

DCM

Dichloromethane, methylene chloride

DIEA, DIPEA

N,N-Diisopropylethylamine

DMAP

4-Dimethylaminopyridine

DMF

Dimethylformamide

DMSO

Dimethyl sulfoxide

DTT

Dithiothreitol

EDC, EDCI

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide

EDT

Ethane-1,2-dithiol

Fmoc

9-Fluorenylmethoxycarbonyl

Gdm

Guanidinium

GDP

Guanosine diphosphate

HATU

2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

HBTU

2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

HEPES

4-(2-Hydroxyethyl)-1-piperazineethanesulfonic acid

HMPA

4-Hydroxymethylphenoxyacetyl

HMPB

4-(4-Hydroxymethyl-3-methoxyphenoxy)butyryl

HOBt

N-Hydroxybenzotriazole

HYCRON

Hydroxycrotyloligoethylene glycol-n-alkanoyl

ivDde

(4,4-Dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl

MCA

Monochloroacetyl

MES-Na

Sodium mercaptoethanesulfonate

MOPS

3-(N-Morpholino)propanesulfonic acid

NIS

N-Iodosuccinimide

NMP

N-Methylpyrrolidone

Pi

Phosphate

Pbf

2,2,4,6,7-Pentamethyldihydrobenzofuran-5-sulfonyl

Phth

Phthaloyl

PTSA

p-Toluenesulfonic acid

PyBOP

Benzotriazole-1-yl-tris-pyrrolidino-phosphonium hexafluorophosphate

SASRIN

Super acid sensitve resin

Su

Succinimidyl

TBAF

Tetrabutylammonium fluoride

TBS

tert-Butyldimethylsilyl

TCEP

Tris(2-carboxyethyl)phosphine

Tf

Trifluoromethanesulfonyl

TFA

Trifluoroacetic acid

TFE

Trifluoro ethanol

TfOH

Trifluoromethanesulfonic acid

THF

Tetrahydrofuran

TIS

Triisopropylsilane

TMS

Trimethylsilyl

Tris

Tris(hydroxymethyl)aminomethane

Troc

2,2,2-Trichloroethoxycarbonyl

Trt

Trityl

Tsoc

Triisopropylsilyloxycarbonyl

Z

Benzyloxycarbonyl

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Copyright information

© Springer-Verlag Berlin Heidelberg 2006

Authors and Affiliations

  1. 1.Institut für ChemieHumboldt-Universität zu BerlinBerlinGermany

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