Ready routes to key myo-inositol component of GPIs employing microbial arene oxidation or Ferrier reaction

Jia, Zhaozhong J.; Olsson, Lars‐Inge; Fraser‐Reid, Bert

doi:10.1039/a800282g

Cited by 35 publications

(18 citation statements)

References 11 publications

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“…Synthesis of the protected optically pure D-myo-inositol building block 7 started from methyl-glucoside. 19,20 The primary alcohol was protected with a trityl group, followed by the overnight per-naphthyl-methylation using 2-(naphthyl)-methyl bromide and NaH (Scheme 1). After removal of the trityl ether, alcohol oxidation with SO 3 -pyridine complex to the aldehyde, and subsequent acetylation produced enol-ester 10.…”

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confidence: 99%

Synthesis of glycosylphosphatidylinositol (GPI)-anchor glycolipids bearing unsaturated lipids

2016

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confidence: 99%

Synthesis of glycosylphosphatidylinositol (GPI)-anchor glycolipids bearing unsaturated lipids

2016

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“…Recently, we developed another synthetic method for 1,2,6- O -differentiated inositol derivatives, starting with methyl α-D-glucopyranoside 14 (Scheme 3) [55], in which a key step was the stereospecific Ferrier rearrangement of 15 to produce 16 [56,57]. Thereafter, the carbonyl group of 16 was stereospecifically reduced with NaBH(OAc) 3 , followed by 1- O -deacetylation to afford 18 .…”

Section: Chemical Synthesis Of Gpis and Related Derivativesmentioning

confidence: 99%

Synthetic Studies of Glycosylphosphatidylinositol (GPI) Anchors and GPI-Anchored Peptides, Glycopeptides, and Proteins

Guo¹

2013

COS

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Glycosylphosphatidylinositol (GPI) anchorage of proteins and glycoproteins onto the cell surface is ubiquitous in eukaryotes, and GPI-anchored proteins and glycoproteins play an important role in many biological processes. To study GPI anchorage and explore the functions of GPIs and GPI-anchored proteins and glycoproteins, it is essential to have access to these molecules in homogeneous and structurally defined forms. This review is focused on the progress that our laboratory has made towards the chemical and chemoenzymatic synthesis of structurally defined GPI anchors and GPI-anchored peptides, glycopeptides, and proteins. Briefly, highly convergent strategies were developed for GPI synthesis and were employed to successfully synthesize a number of GPIs, including those carrying unsaturated lipids and other useful functionalities such as the azido and alkynyl groups. The latter enabled further site-specific modification of GPIs by click chemistry. GPI-linked peptides, glycopeptides, and proteins were prepared by regioselective chemical coupling of properly protected GPIs and peptides/glycopeptides or through site-specific ligation of synthetic GPIs and peptides/glycopeptides/proteins under the influence of sortase A. The investigation of interactions between GPI anchors and pore-forming bacterial toxins by means of synthetic GPI anchors and GPI analogs is also discussed.

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“…The method of Fraser-Reid and co-workers [39] involved the preparation of optically pure, differentially protected myo-inositols from methyl α--glucopyranoside (11, Scheme 2). Compound 11 was transformed into 12 in four steps, which was readily converted into enol acetate 13.…”

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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Ready routes to key myo-inositol component of GPIs employing microbial arene oxidation or Ferrier reaction

Cited by 35 publications

References 11 publications

Synthesis of glycosylphosphatidylinositol (GPI)-anchor glycolipids bearing unsaturated lipids

Synthesis of glycosylphosphatidylinositol (GPI)-anchor glycolipids bearing unsaturated lipids

Synthetic Studies of Glycosylphosphatidylinositol (GPI) Anchors and GPI-Anchored Peptides, Glycopeptides, and Proteins

Chemical Synthesis of GPIs and GPI‐Anchored Glycopeptides

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