Synthesis and structure of a carbohydrate-fused [15]-macrodilactone

Si, Debjani; Peczuh, Mark W.

doi:10.1016/j.carres.2016.08.010

Cited by 4 publications

(2 citation statements)

References 43 publications

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“…24,25 Within this framework, it is worth mentioning the synthesis of unnatural 15-membered macrodilactone-containing glycolipids recently described by Si and Peczuh. 26 In view of its potential biological activity, we believe that ananatoside A (1) could represent an interesting and readily accessible synthetic target for organic chemists.…”

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confidence: 99%

Structural determination of ananatoside A: An unprecedented 15-membered macrodilactone-containing glycolipid from Pantoea ananatis

Gauthier

Lavoie

Piochon

et al. 2019

Carbohydrate Research

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confidence: 99%

Structural determination of ananatoside A: An unprecedented 15-membered macrodilactone-containing glycolipid from Pantoea ananatis

Gauthier

Lavoie

Piochon

et al. 2019

Carbohydrate Research

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“…Using a hexapyranose as the scaffold, a variety of synthetic macrolactones can be prepared depending on the cyclization patterns from different positions of the sugar ring. The lactonization could be introduced at an earlier stage and a different method for the macrocyclization utilized later [ 12 , 15 ]. For instance, the glycomacrolactones with azobenzene functionality have been synthesized through the cyclization from the C-2 to C-3 or C-4 to C-6 positions of D-glucose and D-mannose derivatives.…”

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confidence: 99%

Synthesis of Carbohydrate Based Macrolactones and Their Applications as Receptors for Ion Recognition and Catalysis

2021

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Glycomacrolactones exhibit many interesting biological properties, and they are also important in molecular recognitions and for supramolecular chemistry. Therefore, it is important to be able to access glycomacrocycles with different sizes and functionality. A new series of carbohydrate-based macrocycles containing triazole and lactone moieties have been designed and synthesized. The synthesis features an intramolecular nucleophilic substitution reaction for the macrocyclization step. In this article, the effect of some common sulfonate leaving groups is evaluated for macrolactonization. Using tosylate gave good selectivity for monolactonization products with good yields. Fourteen different macrocycles have been synthesized and characterized, of which eleven macrocycles are from cyclization of the C1 to C6 positions of N-acetyl D-glucosamine derivatives and three others from C2 to C6 cyclization of functionalized D-glucosamine derivatives. These novel macrolactones have unique structures and demonstrate interesting anion binding properties, especially for chloride. The macrocycles containing two triazoles form complexes with copper sulfate, and they are effective ligands for copper sulfate mediated azide-alkyne cycloaddition reactions (CuAAC). In addition, several macrocycles show some selectivity for different alkynes.

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Macrocycles All Aflutter: Substitution at an Allylic Center Reveals the Conformational Dynamics of [13]‐Macrodilactones

Rutledge

Hamlin

Baldisseri

et al. 2017

Chemistry An Asian Journal

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The shapes adopted by large-ring macrocyclic compounds play a role in their reactivity and their ability to be bound by biomolecules. We investigated the synthesis, conformational analysis, and properties of a specific family of [13]-macrodilactones as models of natural-product macrocycles. The features of our macrodilactones enabled us to study the relationship between stereogenic centers and planar chirality through the modular synthesis of new members of this family of macrocycles. Here we report on insights gained from a new [13]-macrodilactone that is substituted at a position adjacent to the alkene in the molecule. Analysis of the compound, in comparison to an α-substituted regioisomer, by using X-ray crystallography, NMR coupling constants, and reaction-product characterization in concert with computational chemistry, revealed that the alkene unit is dynamic. That is, the data support a model in which the alkene in our [13]-macrodilactones oscillates between two conformations. A difference in reactivity of one conformation compared to the other leads to manifestation of this dynamic behavior. The results underscore the local conformational dynamics observed in some natural-product macrocycles, which could have implications for biomolecule binding.

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Synthesis and structure of a carbohydrate-fused [15]-macrodilactone

Cited by 4 publications

References 43 publications

Structural determination of ananatoside A: An unprecedented 15-membered macrodilactone-containing glycolipid from Pantoea ananatis

Structural determination of ananatoside A: An unprecedented 15-membered macrodilactone-containing glycolipid from Pantoea ananatis

Synthesis of Carbohydrate Based Macrolactones and Their Applications as Receptors for Ion Recognition and Catalysis

Macrocycles All Aflutter: Substitution at an Allylic Center Reveals the Conformational Dynamics of [13]‐Macrodilactones

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