Synthesis and NMR Studies of Cyclopeptides Containing a Sugar Amino Acid

Stöckle, Matthias; Voll, Georg; Gunther, Robert A.; Lohof, Elisabeth; Locardi, Elsa; Gruner, Sibylle A. W.; Kessler, Horst

doi:10.1021/ol020138h

Cited by 8 publications

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“…[12][13][14][15][16][17] Members of this class of SAAs have found application in foldamers, [18,19] host-guest studies, [20] and as turn inducers. [21] We suggest SAA 12 as a promising candidate for such applications, due to the rigid nature of the molecule.…”

Section: Introductionmentioning

confidence: 99%

A Conformationally Locked AminomethylC‐Glycoside and Studies on ItsN‐Pyren‐1‐ylcarbonyl Derivative Inserted into Oligodeoxynucleotides

et al. 2006

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A new conformationally locked aminomethyl C-glycoside has been synthesized and incorporated into oligonucleotides (ONs). The applicability of the monomer in post-ON synthesis (i.e., conjugation by organic synthesis performed on ONs attached to resin) has been successfully demonstrated by condensation with pyren-1-ylcarboxylic acid. The abilities of the pyrenyl-derivatized ONs to recognize abasic sites in complementary strands were investigated by thermal denatur-

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Section: Introductionmentioning

confidence: 99%

A Conformationally Locked AminomethylC‐Glycoside and Studies on ItsN‐Pyren‐1‐ylcarbonyl Derivative Inserted into Oligodeoxynucleotides

et al. 2006

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Differently Glycosidated 2‐Amino‐2‐deoxy‐d‐glucopyranosiduronic Acids as Building Blocks in Peptide Synthesis

Kyas

Feigel

2005

Helvetica Chimica Acta

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Seven differently glycosidated sugar amino acids (SSAs) derived from glucosamine have been prepared. Following standard solution-phase peptide-coupling procedures, the glycosidated 2-amino-2-deoxy-d-glucopyranosiduronic acids were condensed with natural amino acids to furnish useful heterodi-and -trimeric building blocks to be used in peptide synthesis. Combinations of these building blocks yielded hetero-oligomeric peptides with two sugar amino acid units in different distances to each other. These were prepared to evaluate the influence of glycosidic side chains on the peptide backbone. Conformations of selected examples were examined by means of ROESY spectroscopy in combination with molecular dynamics (MD) simulations and circulardichroism (CD) studies.

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A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues

et al. 2013

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This compendium focuses on functionalised sugar amino acids (SAAs) and their 3- to 6-membered nitrogen heterocyclic and carbocyclic analogues. The main benefit of using SAAs and their related nitrogen and carbon congeners in the production of peptidomimetics and glycomimetics is that their properties can be readily altered via modification of their ring size, chemical manipulation of their numerous functional groups and fine-tuning of the stereochemical arrangement of their ring substituents. These building blocks provide access to hydrophilic and hydrophobic peptide isosteres whose physical properties allow entry to a region of chemotherapeutic space which is still under-explored by medicinal chemists. These building blocks are also important in providing amino acids whose inherent conformational bias leads to predisposition to secondary structure upon oligomerisation in relatively short sequences. These foldamers, particularly those containing ω-amino acids, provide an additional opportunity to expand access to the control of structures by artificial peptides. The synthesis and biological evaluation of these building blocks in glycomimetics and peptidomimetics systems keep expanding the reach of the glycosciences to the medical sciences, provide a greater outlook onto the wide range of cellular functions of saccharides and their derivatives involved and greater insight into the nature of oligosaccharide and protein folding.

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Synthesis and NMR Studies of Cyclopeptides Containing a Sugar Amino Acid

Cited by 8 publications

References 0 publications

A Conformationally Locked AminomethylC‐Glycoside and Studies on ItsN‐Pyren‐1‐ylcarbonyl Derivative Inserted into Oligodeoxynucleotides

A Conformationally Locked AminomethylC‐Glycoside and Studies on ItsN‐Pyren‐1‐ylcarbonyl Derivative Inserted into Oligodeoxynucleotides

Differently Glycosidated 2‐Amino‐2‐deoxy‐d‐glucopyranosiduronic Acids as Building Blocks in Peptide Synthesis

A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues

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