Cyclo[(6-amino-6-deoxy-d-galactonic acid)4]: a new class of carbopeptoid-cyclodextrin

Mayes, Benjamin A.; Stetz, Rebecca J. E.; Ansell, Christopher W. G.; Fleet, George W. J.

doi:10.1016/j.tetlet.2003.10.104

Cited by 26 publications

(11 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For the synthesis and use of sugar amino acids, see: Smith & Fleet (1999); Gibson et al (2009); Mayes, Stetz et al (2004); Hungerford et al (2000); Jagadeesh et al (2009); Risseeuw et al (2007); Edwards et al (2008). For the synthesis of pentafluorophenyl esters in this series of compounds, see: Mayes, Cowley et al (2004); Mayes, Simon et al (2004).…”

Section: Related Literaturementioning

confidence: 99%

“…Sugar amino acids (SAAs) have been extensively used in the design of peptidomimetics (Smith & Fleet, 1999;Gibson et al, 2009), cyclodextrin mimics (Mayes, Stetz et al, 2004), and foldamers (Hungerford et al, 2000;Jagadeesh et al, 2009). Foldamers provide increased understanding of the factors which induce secondary structures in proteins (Edwards et al, 2008).…”

Section: S1 Commentmentioning

confidence: 99%

See 1 more Smart Citation

Pentafluorophenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate

et al. 2010

View full text Add to dashboard Cite

The title compound, C22H25F5N4O9, is a stable pentafluorophenyl ester intermediate in the synthesis of novel homo-oligomeric structures containing branched carbon chains. The structure is epimeric to the previously characterized dimeric pentafluorophenyl ester with stereochemistry (3R,4R,5R), which was synthesized using d-ribose as starting material. The crystal structure of the title molecule removes any ambiguities arising from the relative stereochemistries of the six chiral centres. Two hydrogen bonds, bifurcating from the NH group, stabilize the crystal: one intramolecular and one intermolecular, both involving O atoms of the methoxy groups. The asymmetric unit contains two independent molecules not related by any pseudo-symmetry operators. The major conformational differences are localized, leading to one molecule being extended compared to the other. The collected crystal was twinned (twin ratio is 0.939:0.061), and the azide group is positionally disordered over two positions in one molecule [occupancy ratio 0.511 (18):0.489 (18)].

show abstract

Section: Related Literaturementioning

confidence: 99%

Section: S1 Commentmentioning

confidence: 99%

Pentafluorophenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate

et al. 2010

View full text Add to dashboard Cite

show abstract

“…Several cyclic homooligomers have now been prepared using oxetane, furanose and pyranose SAAs (Johnson et al, 2006;van Well, Marinelli et al, 2003;Chakraborty et al, 2003); a cyclic hexamer of pyranose SAAs was found to form inclusion complexes akin to those of cyclodextrins (Locardi et al, 2001). A new family of cyclic SAA oligomers, based on acyclic SAAs, has been established (Mayes, Stetz et al, 2004;Mayes, Simon et al, 2004;Mayes, Cowley et al, 2004) and a cyclic dimer of galactose stereochemistry found to interact with probe compounds (Edwards et al, 2005). This family has now been expanded to include heterooligomers which incorporate phenylalanine (Phe).…”

Section: Figurementioning

confidence: 99%

cyclo{[(6-Amino-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonic acid)-(D-Phe)]₂}

et al. 2006

View full text Add to dashboard Cite

show abstract

“…Following the lead of PNAs (peptide nucleic acids), Goodnow et al 43,44 suggested the GNAs (glucopyranosyl nucleic amide) as oligomers of glucosamineuronic acid with nucleobases attached via a N-glycosidic linkage to the anomeric centers. In recent work, Kessler as well as Fleet have prepared a range of cyclic SAA macrolactams, [45][46][47][48] while Gregar and Gervay-Hague 49 have studied linear oligomers derived from amide-linked neuraminic acid analogues. For other examples of SAAs in carbopeptoids, see the comprehensive review on foldamers by Hill et al 50 …”

Section: Figurementioning

confidence: 99%

Carbohydrates in peptide and protein design

Jensen¹,

Brask²

2005

Biopolymers

View full text Add to dashboard Cite

Monosaccharides and amino acids are fundamental building blocks in the assembly of nature's polymers. They have different structural aspects and, to a significant extent, different functional groups. Oligomerization gives rise to oligosaccharides and peptides, respectively. While carbohydrates and peptides can be found conjoined in nature, e.g., in glycopeptides, the aim of this review is the radical redesign of peptide structures using carbohydrates, particularly monosaccharides and cyclic oligosaccharides, to produce novel peptides, peptidomimetics, and abiotic proteins. These hybrid molecules, chimeras, have properties arising largely from the combination of structural characteristics of carbohydrates with the functional group diversity of peptides. This field includes de novo designed synthetic glycopeptides, sugar (carbohydrate) amino acids, carbohydrate scaffolds for nonpeptidal peptidomimetics of cyclic peptides, cyclodextrin functionalized peptides, and carboproteins, i.e., carbohydrate-based proteinmimetics. These successful applications demonstrate the general utility of carbohydrates in peptide and protein architecture. #

show abstract

Cyclo[(6-amino-6-deoxy-d-galactonic acid)4]: a new class of carbopeptoid-cyclodextrin

Cited by 26 publications

References 26 publications

Pentafluorophenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate

Pentafluorophenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate

cyclo{[(6-Amino-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonic acid)-(D-Phe)]₂}

Carbohydrates in peptide and protein design

Contact Info

Product

Resources

About

Cyclo[(6-amino-6-deoxy-d-galactonic acid)4]: a new class of carbopeptoid-cyclodextrin

Cited by 26 publications

References 26 publications

Pentafluorophenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate

Pentafluorophenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate

cyclo{[(6-Amino-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonic acid)-(D-Phe)]2}

Carbohydrates in peptide and protein design

Contact Info

Product

Resources

About

cyclo{[(6-Amino-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonic acid)-(D-Phe)]₂}