Huge (14-, 21-, 28-, 35-, 56- and 70-membered ring) macrocyclic lactams––a novel family of carbopeptoid-cyclodextrins

Mayes, Benjamin A.; Simon, Lieven; Watkin, David J.; Ansell, Christopher W. G.; Fleet, George W. J.

doi:10.1016/j.tetlet.2003.10.103

Cited by 27 publications

(16 citation statements)

References 26 publications

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“…Analysis of the product isolated from the polycondensation reaction by MALDI-TOF mass spectrometry revealed formation of polymeric species. However, this spectrum exhibited a rather particular pattern of signals ( In agreement with the MS, the NMR spectra of the mixture 5 showed clearly that the highest signals maintained a good correlation with the NMR spectra reported for the cyclic trimer of the amino acid 4, which had been synthesized and isolated by Fleet et al 29,30 Also, in agreement with our results, they have shown that polycondensation of the free amino acid 6, under conditions that favored the cyclooligomerization led to the formation of cyclooligomers, being the cyclic trimer the main product. The molecular weight for the linear polymer constituent of 5 was estimated from its MALDI-TOF MS taking into account the m/z value of each peak and its relative intensity (M w = 2028, M n = 1830, and polydispersity = 1.11).…”

Section: Methodssupporting

confidence: 82%

“…However, the 13 C-NMR spectrum of 5 showed a resonance at 74.9 ppm, signal which was absent in the spectrum of 11. Interestingly, similar high field resonances (assigned to C-2) were observed for the cyclic trimer 29 (74.95 ppm) and cyclic tetramer 30 (74.4 ppm) derivatives of 6; whereas in the respective spectra of the linear oligomers, the highest field resonances for carbons bonded to oxygen appeared at 76.5-77.0 ppm. 30 This result seems to bring additional support to the structure assigned for the polycondensation products 5 and 11.…”

Section: Methodssupporting

confidence: 62%

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Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives

Zaliz¹,

Erra‐Balsells²,

Nonami³

et al. 2005

Arkivoc

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Methyl 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate (1), prepared in two steps from D-galactono-1,4-lactone, was hydrolyzed to the corresponding acid 2, which was esterified with phenol (PhOH) in the presence of dicyclohexylcarbodiimide (DCC) to give the phenyl ester 3. Hydrogenolysis of the azide function of 3 yielded the hydrochloride derivative of the amino acid 4. Compound 4 is conveniently substituted for the polycondensation; therefore, this reaction was conducted using DMF as solvent and N,N-diisopropylethylamine as a basic catalyst. The MALDI-TOF mass spectrum of the isolated product (5) indicated that this was a mixture of the cyclic trimer (M + Na + , 793.7) and linear oligomers (from the tetramer to the tetradecamer). To favor the linear polymerization the dimeric amino acid 10 was prepared starting from 2. Thus, hydrogenation of 2 gave the amino acid 6, and treatment of 2 with pentachlorophenol-DCC gave the pentachlorophenyl ester 7. Coupling of 6 with 7 in the presence of DCC gave the dimer 8, which was converted (PhOH, DCC) into 9. Hydrogenolysis of 9 afforded the dimeric amino acid 10, which was polymerized under the conditions employed for 4. The resulting polyamide 11 was highly soluble in common organic solvents, and its molecular weight was established by MALDI-TOF MS and size exclusion chromatography (M w = 2700).

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Section: Methodssupporting

confidence: 82%

Section: Methodssupporting

confidence: 62%

Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives

Zaliz¹,

Erra‐Balsells²,

Nonami³

et al. 2005

Arkivoc

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“…6,10,30 Here we report the study of cyclic dimers by CD and crystallography. The amide bonds enable CD to be used to study the flexibility, stability, and binding features of these systems in an analogous fashion to the technique's application to protein studies.…”

Section: Resultsmentioning

confidence: 99%

“…The syntheses of compounds 1 -4 have been previously reported. 10,30 The stereochemistry of the sugars (when present) and the extent of hydroxyl protection are detailed in Figure 2.…”

Section: Chemicalsmentioning

confidence: 99%

Circular dichroism studies of carbopeptoid-cyclodextrins

et al. 2005

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A series of sugar amino acids, based on open chain sugars, have been oligomerised and cyclised. The resulting cyclic carbopeptoids have been examined for desirable properties such as host-guest chemistry (as in cyclodextrins) or self-assembling properties (e.g., peptide nanotubes). Initial studies of these systems, by circular dichroism and X-ray crystallography, have given valuable insight into their stability and properties. One of the four cyclic species studied was found to interact with ion/molecular probes.

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“…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

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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. #

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Huge (14-, 21-, 28-, 35-, 56- and 70-membered ring) macrocyclic lactams––a novel family of carbopeptoid-cyclodextrins

Cited by 27 publications

References 26 publications

Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives

Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives

Circular dichroism studies of carbopeptoid-cyclodextrins

Carbohydrates in peptide and protein design

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