Clickable Glycopeptoids for Synthesis of Glycopeptide Mimic

Singhamahapatra, Anadi; Sahoo, Laxminarayan; Loganathan, Duraikkannu

doi:10.1021/jo401720s

Cited by 14 publications

(2 citation statements)

References 26 publications

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“…Triazole‐linked glycopeptoid building blocks with β,β, α,β and β,α architectures were synthesised recently (Figure 11),60 but their incorporation in homogeneous β‐peptoids or hybrid α,β‐peptoids was not demonstrated 61…”

Section: β‐Glycopeptoidsmentioning

confidence: 99%

From Glycopeptides to Glycopeptoids

Szekely¹,

Roy²,

Faure³

et al. 2014

Eur J Org Chem

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This review covers the published literature describing the synthesis of glycopeptoids, a family of glycopeptide mimics. Members of this family are composed of an N‐substituted glycine or β‐alanine oligomer backbone linked to one or several carbohydrate moieties at the amide nitrogen atoms. The interest in this class of biomimetics lies in their enhanced proteolytic stability and greater conformational flexibility relative to glycopeptides. This Microreview not only describes the different methods for synthesising glycopeptoids but also discusses their application both as glycopeptidomimetics and glycocluster constructs.

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Section: β‐Glycopeptoidsmentioning

confidence: 99%

From Glycopeptides to Glycopeptoids

Szekely¹,

Roy²,

Faure³

et al. 2014

Eur J Org Chem

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“…In the literature, many diversely functionalized glycoconjugates are reported to be synthesized using a click reaction. [14][15][16] Recently, the synthesis of diversely functionalized "clickable" glycopeptoids 17 and other glycoconjugates, 18,19 such as triazole containing glycolipids, that are potentially useful in the area of chemical biology, were reported. In this present work, a series of novel difunctionalized glycoconjugate in which the sugar molecules were functionalized with azide or alkyne or both groups, which could be used for synthesis of complex glycoconjugates, was synthesized using Cu(I) catalyzed click reactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization

Sahoo

Singhamahapatra

Sahoo

2018

JSCS

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A series of novel 1,3-difunctionalized glycoconjugates were synthesized using a sequence of regioselective functionalization and stereoselective glycosidation of D-glucose and D-GlcNAc. Regioselective C-3 functionalization of sugar molecules was achieved by chemical functionalization of isopropylidene or oxazoline protected sugar derivatives. The structural diversity at the anomeric carbon was explored by stereoselective chemical glycosidation. The oxazoline protected D-GlcNAc derivative gave either pyranose or furanose derivatives on glycosidation depending on the amount of Lewis acid used. The diversely functionalized glycoconjugates with azide or alkyne groups are potentially useful for the synthesis of multifunctionalized complex glycoconjugates via click reactions.

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Sequence Programmable Peptoid Polymers for Diverse Materials Applications

et al. 2015

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Polymer sequence programmability is required for the diverse structures and complex properties that are achieved by native biological polymers, but efforts towards controlling the sequence of synthetic polymers are, by comparison, still in their infancy. Traditional polymers provide robust and chemically diverse materials, but synthetic control over their monomer sequences is limited. The modular and step-wise synthesis of peptoid polymers, on the other hand, allows for precise control over the monomer sequences, affording opportunities for these chains to fold into well-defined nanostructures. Hundreds of different side chains have been incorporated into peptoid polymers using efficient reaction chemistry, allowing for a seemingly infinite variety of possible synthetically accessible polymer sequences. Combinatorial discovery techniques have allowed the identification of functional polymers within large libraries of peptoids, and newly developed theoretical modeling tools specifically adapted for peptoids enable the future design of polymers with desired functions. Work towards controlling the three-dimensional structure of peptoids, from the conformation of the amide bond to the formation of protein-like tertiary structure, has and will continue to enable the construction of tunable and innovative nanomaterials that bridge the gap between natural and synthetic polymers.

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Clickable Glycopeptoids for Synthesis of Glycopeptide Mimic

Cited by 14 publications

References 26 publications

From Glycopeptides to Glycopeptoids

From Glycopeptides to Glycopeptoids

Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization

Sequence Programmable Peptoid Polymers for Diverse Materials Applications

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