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Taxonomic group: protista / Apicomplexa (Phylum: Apicomplexa)
Host organism: Homo sapiens
Associated disease: malaria due to Plasmodium falciparum [ICD11: 1F40

, ICD11: XN69B

]

NCBI PubMed ID: 22794184
Publication DOI: 10.1016/B978-0-12-396527-1.00004-8
Journal NLM ID: 0240537
Correspondence: zwguo

chem.wayne.edu
Institutions: Department of Chemistry, Wayne State University, Detroit, MI, USA

Many eukaryotic cell-surface proteins and glycoproteins are anchored to the plasma membrane by glycosylphosphatidylinositols (GPIs), a family of glycolipids that are post-translationally attached to proteins at their C-termini. GPIs and GPI-anchored proteins play important roles in many biological and pathological events, such as cell recognition and adhesion, signal transduction, host defense, and acting as receptors for viruses and toxins. Chemical synthesis of structurally defined GPI anchors and GPI derivatives is a necessary step toward understanding the properties and functions of these molecules in biological systems and exploring their potential therapeutic applications. In the first part of this comprehensive article on the chemical synthesis of GPIs, classic syntheses of naturally occurring GPI anchors from protozoan parasites, yeast, and mammals are covered. The second part of the article focuses on recent diversity-oriented strategies for the synthesis of GPI anchors containing unsaturated lipids, 'click chemistry' tags, and highly branched and modified structures.

synthesis, carbohydrate, glycolipid, glycosylphosphatidylinositol (GPI) anchor, inositol

Structure type: oligomer
Location inside paper: p. 178, scheme 37, compound 203
Compound class: GPI-anchor
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141807,IEDB_141829,IEDB_141830,IEDB_141832,IEDB_143632,IEDB_144983,IEDB_151531,IEDB_152206,IEDB_153220,IEDB_176772,IEDB_474450,IEDB_534865,IEDB_76933,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

Synthetic data: chemical
Comments, role: review; synthesis of P. falciparum GPI anchor 203 by the Seeberger group

NCBI Taxonomy refs (TaxIDs): 5833
Show glycosyltransferases

There is only one chemically distinct structure:

CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)O[C@@H]1[C@@H](O[C@H]2O[C@H](CO)[C@@H](O[C@H]3O[C@H](CO[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H](COP(=O)(O)OCCN)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O)[C@@H](O)[C@H](O)[C@@H]3O)[C@H](O)[C@H]2N)[C@H](O)[C@@H](O)[C@H](O)[C@@H]1OC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC

SVG MW SMILES 3D mol Ionize