Preparation of bifunctional isocyanate hydroxamate linkers: synthesis of carbamate and urea tethered polyhydroxamic acid chelators

Fernando, Rasika; Shirley, Jonathan M.; Torres, Emilio Alberto Ortíz; Jacobs, Hollie K.; Gopalan, Aravamudan S.

doi:10.1016/j.tetlet.2012.09.025

Cited by 2 publications

(2 citation statements)

References 49 publications

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“…107 However, resistance of phthaloyl or carbamate protected hydroxylamines to hydrogenolysis (catalysed by Pd/C) was also observed. 62,73,83,108,109 In contrast to HF, Bu 4 NF is able to induce N-O cleavage during the desilylation reaction. 110 Under basic conditions, the cleavage of N-O bonds in tri-substituted hydroxylamines is favoured by the formation of a carbanion adjacent to either nitrogen or oxygen atoms.…”

Section: Chemical and Physicochemical Properties Of Hydroxylaminesmentioning

confidence: 99%

N–O linkage in carbohydrates and glycoconjugates

Chen

Xie

2016

Org. Biomol. Chem.

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The importance of oligosaccharides and their conjugates in various biological and pathological processes has stimulated growing interest in the development of (neo)glycoconjugates. Thanks to its high nucleophilicity, hydroxylamine has been employed as a powerful chemoselective ligation tool. Great effort has been focused on carbohydrates bearing aminooxy or N-hydroxy amino groups for organic synthesis, glycobiology and drug discovery. This review provides an overview of N-O linked carbohydrates and glycoconjugates, focusing particularly on the synthetic methodologies and chemical and physicochemical properties as well as biological and medical applications of N-glycosyl and O-glycosyl hydroxylamines, N-hydroxy amino and O-amino sugar as well as sugar aminooxy acid derivatives.

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Section: Chemical and Physicochemical Properties Of Hydroxylaminesmentioning

confidence: 99%

N–O linkage in carbohydrates and glycoconjugates

Chen

Xie

2016

Org. Biomol. Chem.

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“…26 TREN has been a highly used tripodal platform to prepare hydroxamates and hydroxypyridinones that show strong binding to iron. 27 …”

Section: Resultsmentioning

confidence: 99%

Preparation of 3-benzyloxy-2-pyridinone functional linkers: tools for the synthesis of 3,2-hydroxypyridinone (HOPO) and HOPO/hydroxamic acid chelators

et al. 2015

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In contrast to 2,3-dihydroxypyridine, the 3-benzyloxy protected derivative, 2, undergoes facile alkylation at ambient temperatures with a variety of functionalized alkyl halides in good yields. This alkylation has been used to prepare a number of linkers that permit the attachment of 3,2-HOPO moieties onto various scaffolds using a wide range of coupling methods. The Mitsunobu reaction of 2 with representative alcohols was found to be of limited value due to competing O-alkylation that led to product mixtures. The phthalimide 3j can be converted in two steps to HOPO isocyanate 6 in excellent yields. Isocyanate 6 can be coupled to amines at room temperature or to alcohols in refluxing dichloroethane to obtain the corresponding urea or carbamate linked ligand systems. The coupling of isocyanate 6 with TREN followed by deprotection gave the tris-HOPO 10, an interesting target as it has both cationic and anionic binding sites. The HOPO hydroxylamine linker 11 was shown to be especially valuable as its coupling with carboxylic acids proceeds with the concomitant generation of an additional hydroxamate ligand moiety in the framework. The utility of this linker was shown by the preparation of two mixed HOPO-hydroxamate chelators, 16 and 19, based on the structure of desferrioxamine, a well-known trihydroxamate siderophore.

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Preparation of bifunctional isocyanate hydroxamate linkers: synthesis of carbamate and urea tethered polyhydroxamic acid chelators

Cited by 2 publications

References 49 publications

N–O linkage in carbohydrates and glycoconjugates

N–O linkage in carbohydrates and glycoconjugates

Preparation of 3-benzyloxy-2-pyridinone functional linkers: tools for the synthesis of 3,2-hydroxypyridinone (HOPO) and HOPO/hydroxamic acid chelators

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