<i>cyclo</i>Saligenyl‐mannose‐1‐monophosphates as a New Strategy in CDG‐Ia Therapy: Hydrolysis, Mechanistic Insights and Biological Activity

Muus, Ulrike; Kranz, Christian; Marquardt, Thorsten; Meier, Chris

doi:10.1002/ejoc.200300681

Cited by 18 publications

(6 citation statements)

References 17 publications

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“…In humans, mutations in PMM genes cause the most common of the congenital deficiencies in glycosylation, severe inherited diseases that result from defective mannosylation of glycoproteins. Different membrane-permeable derivatives of mannose-1-phosphate have been synthesised as prodrugs that bypass the block in the pathway to GDPmannose (Eklund et al, 2005;Muus et al, 2004). The negative charges on the phosphate group were neutralised with acetoxymethyl or cyclosaligenyl groups whereas the sugar hydroxyls were esterified with acetyl or ethylcarbonate groups to increase hydrophobicity.…”

Section: Discussionmentioning

confidence: 99%

Phosphomannose isomerase and phosphomannomutase gene disruptions in Streptomyces nodosus: Impact on amphotericin biosynthesis and implications for glycosylation engineering

Lochlainn

Caffrey

2009

Metabolic Engineering

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Section: Discussionmentioning

confidence: 99%

Phosphomannose isomerase and phosphomannomutase gene disruptions in Streptomyces nodosus: Impact on amphotericin biosynthesis and implications for glycosylation engineering

Lochlainn

Caffrey

2009

Metabolic Engineering

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“…To complement the low M1P concentration in CDG-Ia patients, other possible modes of delivery must be explored. Covering the hydrophilic phosphate and hydroxyl groups with hydrophobic protection groups has been tested in cell culture systems [80][81][82] and increase the intracellular concentration of M1P. After penetrating the cell membrane, the compounds are hydrolyzed by intracellular esterases (or self-decompose), yielding free M1P and free protecting groups.…”

Section: Figmentioning

confidence: 99%

The congenital disorders of glycosylation: A multifaceted group of syndromes

Eklund

Freeze

2006

Neurotherapeutics

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Summary:The congenital disorders of glycosylation (CDG) are a rapidly expanding group of metabolic syndromes with a wide symptomatology and severity. They all stem from deficient N-glycosylation of proteins. To date the group contains 18 different subtypes: 12 of Type I (disrupted synthesis of the lipid-linked oligosaccharide precursor) and 6 of Type II (malfunctioning trimming/processing of the protein-bound oligosaccharide). Main features of CDG involve psychomotor retardation; ataxia; seizures; retinopathy; liver fibrosis; coagulopathies; failure to thrive; dysmorphic features, including inverted nipples and subcutaneous fat pads; and strabismus. No treatment currently is available for the vast majority of these syndromes (CDG-Ib and CDG-IIc are exceptions), even though attempts to synthesize drugs for the most common subtype, CDG-Ia, have been made. In this review we will discuss the individual syndromes, with focus on their neuronal involvement, available and possible treatments, and future directions.

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“…The intermediate (82) also breaks down by two other independent reactions; one involves intramolecular displacement of aryloxide ion (83) Various Lewis acids MX n have been evaluated as catalysts for the phosphoryl transfer, the most efficient being TiCl 4 (Scheme 21). 50 Physical and kinetic analysis of the cooperative role of metal ions in the catalysis of 2-hydroxypropyl-4-nitrophenyl phosphate (HPNP) cleavage by a dinuclear Zn(II) complex (90) have been reported. 46 A number of N-phosphoryl oxazolidinones (85) have been prepared and developed as alternative phosphorylating agents suitable for a variety of representative alcohols.…”

Section: Scheme 13mentioning

confidence: 99%

“…85 A superior class of nitroaryl phosphoroamides (167), (168) and (169) as potential prodrugs for nitroreductase-mediated enzyme-prodrug therapy has been developed. 90 The modified receptor antagonist (177) has been synthesized. The excellent biological activity of these compounds correlates well with their substrate activity for E coli nitroreductase.…”

Section: Scheme 41mentioning

confidence: 99%

Organophosphorus Chemistry

Hall

Bricklebank

Grampel³

et al. 2006

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Organophosphorus compounds are ubiquitous in nature, and due to their innate chemical properties, serve a fundamental role in a number of important fields. Among the more prominent features that elevate their status as a unique and versatile class of compounds, include variable oxidation states, multivalency, asymmetry and metal-binding properties. Their presence in bioactive natural products, endogenous biomolecules, small molecule therapeutic agents and pro-drugs substantiates their role in modern synthetic chemistry and chemical biology. Moreover, their central use as ligands and effectors in asymmetric catalysis, as well as key functional groups for the development of new synthetic methods, has taken the field to new heights. This Thematic Series highlights and details some of the novel methods that are advancing the field of organophosphorus chemistry.The Thematic Series covers topics that range from new synthetic methods and phosphorus-based ligands in asymmetric catalysis to bisphosphonates as promising enzyme inhibitors. More specifically, the Thematic Series spans new methods in C-P bond formation, chiral phosphines in nucleophilic organocatalysis, chiral N-phosphinyl auxiliaries, cyclic phosphonamide reagents in the total synthesis of natural products, phosphinate-containing heterocycles, new routes to phosphinoyl-indoles and phosphinoyl-isocoumarins and new chemistries of H-phosphonates. The Thematic Series also details work on new metathesis-based reactions of vinyl phosphonates and phosphate tethers, novel phosphorus-based ligands in asymmetric catalysis, novel rasta resin-triphenylphosphine oxides and their use as recyclable heterogeneous reagents, the Atherton-Todd reaction, cyclic phosphonium ionic liquids with distinct properties, photo-removable phosphate protecting groups, new methods of C-H functionalization using phosphoryl-related directing groups, the exciting chemistry of substituted phosphanylidenecarbenes and phosphoryl azides, and bisphosphonate ethers as promising inhibitors of geranylgeranyl diphosphate synthase (GGDPS).The articles and reviews capture the emerging potential of organophosphorus compounds and exciting opportunities in the field, and hopefully, will inspire and motivate investigators in the field to investigate new chemistry in this area. Taken collectively, organophosphorus chemistry embodies a broad, vibrant and continual growing scientific area with this Thematic Series highlighting recent advances in the field. We are grateful and indebted to the authors for their hard work and exciting contri-

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cycloSaligenyl‐mannose‐1‐monophosphates as a New Strategy in CDG‐Ia Therapy: Hydrolysis, Mechanistic Insights and Biological Activity

Cited by 18 publications

References 17 publications

Phosphomannose isomerase and phosphomannomutase gene disruptions in Streptomyces nodosus: Impact on amphotericin biosynthesis and implications for glycosylation engineering

Phosphomannose isomerase and phosphomannomutase gene disruptions in Streptomyces nodosus: Impact on amphotericin biosynthesis and implications for glycosylation engineering

The congenital disorders of glycosylation: A multifaceted group of syndromes

Organophosphorus Chemistry

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