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Glycoscience pp 1697–1731Cite as

Chemical Synthesis of Glycosylphosphatidylinositol (GPI) Anchors and GPI-Linked Structures

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Abstract

Glycosylphosphatidylinositols (GPIs) are a class of natural glycolipids that are ubiquitously expressed by eukaryotic cells. One of the fundamental functions of GPIs is to anchor proteins, glycoproteins, and other molecules onto cell surfaces. The structures of GPIs are diverse and heterogeneous. To obtain homogeneous and well-defined GPIs for various studies, the chemical synthesis of GPIs has become a hot topic. This chapter summarizes the recent progress in the chemical synthesis of GPIs as well as related structures, such as the GPI-linked peptides and glycopeptides.

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Abbreviations

Ac:

acetyl

AChE:

human acetylcholinesterase

acyl-CoA:

acyl coenzyme A 

AG:

acyl glycerol

AIBN:

azoisobutyronitrile

alk-AG:

alkyl acyl glycerol

All:

allyl

Bn:

benzyl

Boc:

t-butyloxycarbonyl

t-Bu:

t-butyl

Bz:

benzoyl

CAM:

camphanic

camph:

camphylidene

Cbz:

benzyloxycarbonyl

ClAc:

2‑chloroacetyl

m-CPBA:

m-chloroperbenzoic acid

DCC:

N,N′-dicyclohexylcarbodiimide

Dol-P-Man:

dolicholphosphomannose

EDC:

1-[3-(dimethylamino)propyl]-3‑ethylcarbodiimide hydrochloride

FBP:

folate binding protein

Fmoc:

9‑fluorenylmethoxycarbonyl

Gal:

galactose

GIPL:

glycoinositol phospholipids

Glc:

glucose

GlcNAc:

N‑acetylglucosamine

GlcNH2 :

glucosamine

GPI:

glycosylphosphatidylinositol

HOBt:

N‑hydroxybenzotriazole

KLH:

keyhole limpet haemocyanin

Lev:

levulinoyl

LHMDS:

lithium hexamethyldisilazide

LPG:

lipophosphoglycan

Man:

mannose

MBn:

4‑methoxybenzyl

Me:

methyl

Mnt:

menthyloxycarbonyl

MPh:

4‑methoxyphenyl

NeuNAc:

N‑acetyl neuraminic acid (sialic acid)

NIS:

N‑iodosuccinimide

PA:

phenoxyacetyl

PARP:

procyclic acidic repetitive protein

Pent:

pentenyl

Ph:

phenyl

Phth:

phthalyl

PI:

phosphatidylinositol

PI-PLC:

PI-specific phospholipase C

P-OEtNH2 :

phosphoethanolamine

i-Pr:

iso-propyl

Prp:

prion protein

PsA:

prespore‐specific antigen

TBDMS:

t-butyldimethylsilyl

TBDPS:

t-butyldiphenylsilyl

TClAc:

trichloroacetyl

TFA:

trifluoroacetic acid

TIPDS:

1,1,3,3‑tetraisopropyldisiloxyl

TIPS:

triisopropylsilyl

TPAP:

tetrapropylammonium perruthenate

Trt:

trityl (triphenylmethyl)

VSG:

variant surface glycoprotein

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Acknowledgement

ZG thanks his devoted students and research associates who have made great contributions to our research programs. We appreciate the financial supports for our research from the US National Science Foundation (CHE-0407144) and National Institutes of Health (R01‑CA95142).

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Authors and Affiliations

  1. Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI, 48202, USA

    Zhongwu Guo & Lee Bishop

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  1. Zhongwu Guo
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  2. Lee Bishop
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Editors and Affiliations

  1. Natural Products and Glycotechnology Research Institute Inc., North Caroline State University, 4118 Swarthmore Road, Durham, NC, 27707, USA

    Bertram O. Fraser-Reid Prof. Dr.

  2. University Graduate School of Science and Engineering, 3-4-1 Ohkubo, Shinjuku, Tokyo, Japan

    Kuniaki Tatsuta Prof. Dr.

  3. Faculty of ScienceDepartment of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany

    Joachim Thiem Prof. Dr.

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Guo, Z., Bishop, L. (2008). Chemical Synthesis of Glycosylphosphatidylinositol (GPI) Anchors and GPI-Linked Structures. In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_42

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