Conformational studies of oligomeric oxetane-based dipeptide isosteres derived fromL-rhamnose orD-xylose

Sm, Johnson; Jenkinson, Sarah F.; Pérez-Victoria, Ignacio; Edwards, Alison A.; Claridge, Timothy D. W.; Tranter, George E.; Fleet, George W. J.; Jones, J. H.

doi:10.1002/psc.658

Cited by 19 publications

(4 citation statements)

References 14 publications

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“…On the other hand, the trans -oxetane amino acid oligomers did not show any defined secondary structures. By contrast, trans -oxetane amino acid oligomers with a bulky 3-( tert -butyldimethylsilyl)oxy (3-OTBS) substituent did display a defined conformation in chloroform and 2,2,2-trifluoroethanol, enforced through steric interactions without the influence of H-bonding . Cyclic tetrameric derivatives have also been prepared …”

Section: Synthesis Of Oxetane Derivatives By Intramolecular Cyclizationmentioning

confidence: 99%

“…By contrast, transoxetane amino acid oligomers with a bulky 3-(tertbutyldimethylsilyl)oxy (3-OTBS) substituent did display a defined conformation in chloroform and 2,2,2-trifluoroethanol, enforced through steric interactions without the influence of Hbonding. 188 Cyclic tetrameric derivatives have also been prepared. 189 Oxetanes have also been incorporated as side chains in βamino acids for the synthesis and conformational analysis of the foldamers they might adopt in solution.…”

Section: Synthesis Of Oxetane Derivatives By Intramolecular Cyclizationmentioning

confidence: 99%

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Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

et al. 2016

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The four-membered oxetane ring has been increasingly exploited for its contrasting behaviors: its influence on physicochemical properties as a stable motif in medicinal chemistry and its propensity to undergo ring-opening reactions as a synthetic intermediate. These applications have driven numerous studies into the synthesis of new oxetane derivatives. This review takes an overview of the literature for the synthesis of oxetane derivatives, concentrating on advances in the last five years up to the end of 2015. These methods are clustered by strategies for preparation of the ring and further derivatization of preformed oxetane-containing building blocks. Examples of the use of oxetanes in medicinal chemistry are reported, including a collation of oxetane derivatives appearing in recent patents for medicinal chemistry applications. Finally, examples of oxetane derivatives in ring-opening and ring-expansion reactions are described.

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Section: Synthesis Of Oxetane Derivatives By Intramolecular Cyclizationmentioning

confidence: 99%

Section: Synthesis Of Oxetane Derivatives By Intramolecular Cyclizationmentioning

confidence: 99%

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

et al. 2016

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“…The results showed that 6-deoxy-L-altronate, D-fuconate and 6-deoxy-D-gulonate oligomers are characterised by irregular non-hydrogen bonded conformations whereas L-rhamnoate and D-lyxonate oligomers have regular conformations governed by sterical interactions [50]. In contrast to the δ-2,4- trans -oxetane-SAA oligomers, the δ-2,4- cis -oxetane-L-ribonate tetramer and hexamer adopted a repeating β-turn structure [51] dictated by internal 10-membered hydrogen bonded rings.…”

Section: Reviewmentioning

confidence: 99%

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

Blanco¹,

Ortega‐Caballero²,

Fernández³

2010

Beilstein J. Org. Chem.

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SummaryOligosaccharides are currently recognised as having functions that influence the entire spectrum of cell activities. However, a distinct disadvantage of naturally occurring oligosaccharides is their metabolic instability in biological systems. Therefore, much effort has been spent in the past two decades on the development of feasible routes to carbohydrate mimetics which can compete with their O-glycosidic counterparts in cell surface adhesion, inhibit carbohydrate processing enzymes, and interfere in the biosynthesis of specific cell surface carbohydrates. Such oligosaccharide mimetics are potential therapeutic agents against HIV and other infections, against cancer, diabetes and other metabolic diseases. An efficient strategy to access this type of compounds is the replacement of the glycosidic linkage by amide or pseudoamide functions such as thiourea, urea and guanidine. In this review we summarise the advances over the last decade in the synthesis of oligosaccharide mimetics that possess amide and pseudoamide linkages, as well as studies focussing on their supramolecular and recognition properties.

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“…There were two exceptions to this: the L L-rhamnoate 3 and D D-lyxonate 4, both of which exhibited an ordered structure which was not stabilised by hydrogen-bonds but was seen to be a result of steric interactions enforced by the bulky tert-butyldimethylsilyl protecting groups. 8 Herein, we report investigations into the secondary structural preferences of homo-oligomers derived from d-2,4-cis-oxetane amino acids 15 (Fig. 2), the synthesis of which was described in a preceding paper.…”

Section: Introductionmentioning

confidence: 99%