An unsaturated peptidomimetic assembly derived from a carbohydrate

Chung, Ying‐Kit; Claridge, Timothy D. W.; Fleet, George W. J.; Sm, Johnson; Jones, J. H.; Lumbard, Keith W.; Stachulski, Andrew V.

doi:10.1002/psc.488

Cited by 13 publications

(3 citation statements)

References 14 publications

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“…1). [6][7][8][9][10] Because of the high degree of functionality present, the amine function can be incorporated at several positions in the scaffold for preparation of analogues, such as of a, b, g, and d-amino acids. Furthermore, the limitations of stereo-control of glycosidic linkages can be circumvented by replacement of the glycosidic linkage by linkages using the acid and amine functions.…”

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confidence: 99%

Classification of conformation for sugar amino acid systems using chiroptical spectroscopy

2006

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A number of structurally related sugar amino acid systems have been examined by chiroptical methods to aid interpretation of their conformational preference. The use of circular dichroism, in addition to NMR and solution IR, has enabled classification of the conformations adopted by sugar amino acid systems as hydrogen-bonded regular, non-hydrogen-bonded regular, and non-hydrogen-bonded irregular. A set of tetrameric SAAs are examined and the effect of change in primary structure related to conformation.

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Classification of conformation for sugar amino acid systems using chiroptical spectroscopy

2006

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“…4) [29]. Analogously, NMR and IR data of a β(1→6)-linked unsaturated glycamino acid tetramer showed a turn-like structure in chloroform solution [31]. …”

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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“…It is well known that oligomers of many carbohydratederived peptidomimetics have the ability to display novel secondary structures. For example, the 'tetramer' of the unsaturated pyranoid system 1 is thought to display a turn-like conformation in chloroform solution [1], whilst the 'octamer' of the furanoid system 2 adopts a left-handed helical conformation [2,3] (see Figure 1). Oxetane-based amino acids are comparatively novel; consequently few conformational studies have been performed on oligomers of these systems.…”

Section: Introductionmentioning

confidence: 99%

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

Jenkinson

Pérez-Victoria

et al. 2005

J. Peptide Sci.

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Conformational investigations have been undertaken on oligomers (dimers, tetramers, hexamers) of five closely related oxetane-based dipeptide isosteres. All the oligomers were subjected to a range of studies by NMR, FT-IR and CD spectroscopy. The oligomers derived from methyl 2,4-anhydro-5-azido-3-O-tert-butyldimethylsilyl-5-deoxy-L-rhamnonate 'monomer' all exhibited evidence of ordered conformations in chloroform and 2,2,2-trifluoroethanol (TFE) solution. 5-Acetamido and N-methylamide derivatives of the L-rhamnonate 'monomer', along with a 'dimer' lacking silyl protection at C-3, were synthesized to ascertain the role of intramolecular interactions. This led to the conclusion that, for the L-rhamnonate oligomers, steric interactions govern the conformational preference observed. The equivalent silyl-protected D-lyxonate oligomers gave ordered CD spectra in TFE solution, but NMR and FT-IR spectroscopy in chloroform solution suggested an irregular, non-hydrogen bonded system. The remaining silyl-protected 6-deoxy-L-altronate, 6-deoxy-D-gulonate and D-fuconate oligomers appear to be characterized by their lack of ordered conformation in TFE and chloroform solution.

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An unsaturated peptidomimetic assembly derived from a carbohydrate

Cited by 13 publications

References 14 publications

Classification of conformation for sugar amino acid systems using chiroptical spectroscopy

Classification of conformation for sugar amino acid systems using chiroptical spectroscopy

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

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

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