Employing BINOL‐Phosphoroselenoyl Chloride for Selective Inositol Phosphorylation and Synthesis of Glycosyl Inositol Phospholipid from <i>Entamoeba histolytica</i>

Aiba, Toshihiko; Suehara, Sae; Choy, Siew Ling; Maekawa, Yuuki; Lotter, Hannelore; Murai, Toshiaki; Inuki, Shinsuke; Fukase, Koichi; Fujimoto, Yukari

doi:10.1002/chem.201701298

Cited by 16 publications

(7 citation statements)

References 36 publications

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“…417 An evaluation of related phosphorus(V)based electrophiles revealed that the highest selectivity (1-OH vs 3-OH) was obtained using phosphorochloridoselenoate 341. 418 These methods were used to prepare inositol phospholipids from the protozoan parasite Entamoeba histolytica.…”

Section: Phosphorylation Of Inositolsmentioning

confidence: 99%

“…A BINOL-derived chiral phosphitylating agent has been used to achieve the desymmetrization of protected myo -inositol 338 (Scheme ). An evaluation of related phosphorus(V)-based electrophiles revealed that the highest selectivity (1-OH vs 3-OH) was obtained using phosphorochloridoselenoate 341 . These methods were used to prepare inositol phospholipids from the protozoan parasite Entamoeba histolytica.…”

Section: Reactions With Phosphorus-centered Electrophilesmentioning

confidence: 99%

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Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

2018

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Methods for site-selective transformations of hydroxyl groups in carbohydrate derivatives are reviewed. The construction of oligosaccharides of defined connectivity hinges on such transformations, which are also needed for the preparation of modified or non-natural sugar derivatives, the installation of naturally occurring postglycosylation modifications, the selective labeling or conjugation of carbohydrate derivatives, and the preparation of therapeutic agents or research tools for glycobiology. The review begins with a discussion of intrinsic factors and processes that can influence selectivity in reactions of unprotected or partially protected carbohydrate derivatives, followed by a description of transformations that engage two OH groups in cyclic adducts (acetals, ketals, boronic esters, and related species). An overview of the various classes of site-selective transformations of OH groups in sugars is then provided: the reactions discussed include esterification, thiocarbonylation, alkylation, glycosylation, arylation, silylation, phosphorylation, sulfonylation, sulfation, and oxidation. Emphasis is placed on recently developed methods that employ reagent or catalyst control to achieve otherwise challenging transformations or site-selectivities.

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Section: Phosphorylation Of Inositolsmentioning

confidence: 99%

Section: Reactions With Phosphorus-centered Electrophilesmentioning

confidence: 99%

Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

2018

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“…Here, we used the 1,1′‐bi‐2‐naphthol (BINOL)‐derived phosphorylation reagents reported by Murai et al. ; [16, 17] 1D‐ myo ‐inositol‐3/1‐phosphate 4 / 7 was selectively synthesized from myo ‐inositol ( 8 ). In this synthetic strategy, early‐stage chiral differentiation of inositol by regioselective phosphorylation allowed straightforward synthesis without the use of unnecessary chiral auxiliaries or tedious and unreliable diastereomer separation.…”

Section: Resultsmentioning

confidence: 99%

Structural Determination and Chemical Synthesis of the N‐Glycan from the Hyperthermophilic Archaeon Thermococcus kodakarensis

et al. 2023

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Asparagine‐linked protein glycosylations (N‐glycosylations) are one of the most abundant post‐translational modifications and are essential for various biological phenomena. Herein, we describe the isolation, structural determination, and chemical synthesis of the N‐glycan from the hyperthermophilic archaeon Thermococcus kodakarensis. The N‐glycan from the organism possesses a unique structure including myo‐inositol, which has not been found in previously characterized N‐glycans. In this structure, myo‐inositol is highly glycosylated and linked with a disaccharide unit through a phosphodiester. The straightforward synthesis of this glycan was accomplished through diastereoselective phosphorylation and phosphodiester construction by SN2 coupling. Considering the early divergence of hyperthermophilic organisms in evolution, this study can be expected to open the door to approaching the primitive function of glycan modification at the molecular level.

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“…In the meantime, other groups have developed related approaches using cyclic asymmetric P-amidites or P-chloridates for desymmetrization. [45][46][47]…”

Section: Account Syn Lettmentioning

confidence: 99%

The Hitchhiker’s Guide to Organophosphate Chemistry

Jessen

2018

Synlett

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Phosphate esters and anhydrides are abundant motifs in biologically important molecules. Their chemical synthesis, modification, and purification are still challenging tasks often restricted to specialized laboratories. The isolation and analytical characterization of novel highly charged (poly)phosphorylated natural products comes with many challenges but also opportunities. Understanding the in vivo function of such molecules is another central endeavor. More often than not, studies into the function of charged metabolites are hampered by insufficient cellular uptake and thus delivery technologies are in high demand. Overall, research in this field requires several complementary approaches. This account discusses selected examples of some emerging technologies in organophosphate chemistry, with a focus on recent achievements in the authors laboratory usually in the context of diverse collaborative efforts.1 Prologue2 Introduction3 The Inositol Phosphates and Pyrophosphates3.1 Novel Synthetic Approaches3.2 Stereochemical Assignment3.3 A Protecting Group Concept for Phosphates3.4 Cellular Delivery3.5 Selected Examples of New Biology4 Nucleotides4.1 Iterative Phosphorylation4.2 Bidirectional Phosphorylation5 Conclusion6 Outlook

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Employing BINOL‐Phosphoroselenoyl Chloride for Selective Inositol Phosphorylation and Synthesis of Glycosyl Inositol Phospholipid from Entamoeba histolytica

Cited by 16 publications

References 36 publications

Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

Structural Determination and Chemical Synthesis of the N‐Glycan from the Hyperthermophilic Archaeon Thermococcus kodakarensis

The Hitchhiker’s Guide to Organophosphate Chemistry

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