A ready, convergent synthesis of the heptasaccharide GPI membrane anchor of rat brain Thy-1 glycoprotein

Udodong, Uko E.; Madsen, Robert; Roberts, Carmichael; Fraser‐Reid, Bert

doi:10.1021/ja00070a048

Cited by 62 publications

(20 citation statements)

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“…The Fraser-Reid group published several synthetic studies on GPI partial structures 38,65–69 prior to the 1995 communication by Campbell and Fraser-Reid describing the synthesis of a rat brain Thy-1 GPI anchor, which constituted the first total synthesis of a mammalian GPI and the third total synthesis in general of a GPI. 70 The Thy-1 GPI glycan contains an additional phosphoethanolamine group at the O-2 position of Man-I (a common modification in mammalian GPIs), as well as GalNAc and Man components attached to the O-4 position of Man-I and the O-2 position of Man-III, respectively.…”

Section: Classic Approaches To Gpi Synthesismentioning

confidence: 99%

Chemical Synthesis of Glycosylphosphatidylinositol Anchors

Swarts

Guo

2012

Advances in Carbohydrate Chemistry and Biochemistry

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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.

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Section: Classic Approaches To Gpi Synthesismentioning

confidence: 99%

Chemical Synthesis of Glycosylphosphatidylinositol Anchors

Swarts

Guo

2012

Advances in Carbohydrate Chemistry and Biochemistry

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“…Since then, a number of groups have synthesized several high-profile GPIs, such as the GPIs of T. brucei by Ley, [25,26] Rat brain Thy-1 by Fraser-Reid [27,28] and Schmidt, [29] S. cerevisiae and T. gondii by Schmidt, [30Ϫ32] P. falciparum by Fraser-Reid [33] and Seeberger, [34,35] and human sperm CD52 by Guo. [36,37] There have also been numerous synthetic studies of the partial and core structures of GPIs, many of which have been covered in Gigg and Gigg's review.…”

Section: Synthesis Of Gpismentioning

confidence: 99%

“…Two strategies were established to resolve the enantiomers of the inositol derivatives. One is based on the linkage of inositol derivatives to a chiral reagent and separation of the resultant diastereoisomers, which has been successfully employed by Fraser-Reid, [27,28] Ley, [25,26] MartinLomas, [42,43] Ogawa, [24,44,45] Schmidt [30,46,47] and so on in their GPI syntheses. The other strategy, developed by Gou et al, [48] makes use of enantioselective enzymatic reactions.…”

Section: Synthesis Of Discriminated Inositolsmentioning

confidence: 99%

Chemical Synthesis of GPIs and GPI‐Anchored Glycopeptides

Guo

Bishop

2004

Eur J Org Chem

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This microreview summarizes some recent progress in the study of glycosylphosphatidylinositols (GPI), focusing on the strategies established for the synthesis of optically pure myoinositol derivatives and complex GPIs and GPI conjugates. Although in the past decade many GPIs have been achieved by linear, convergent and solid-phase synthesis, the GPIs with 2-O-acylated inositol residues and the GPI conjugates of peptides and glycopeptides have not been accomplished

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“…In the previous reports, formation of myoinositol β-glucosaminides was achieved by using the Koenigs-Knorr (6)> glycosyl fluoride (7) and tricWoroacetirnidate (8) methods, as well as npentenylglycosyl donors (9).…”

Section: Syntheses Of Phosphatidylinositol β-D-glucosaminidesmentioning

confidence: 99%