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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- 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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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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DOI: https://doi.org/10.1007/978-3-540-30429-6_42
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