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• W1949089686 abstract "Solution conformation and calcium binding properties have been investigated for the two cyclic octapeptides cyclo(-D-Thr-D-Val(Thz)-Ile-)2 (4) and cyclo(-Thr-Gly(Thz)-Ile-Ser-Gly(Thz)-Ile-) (5) and the results are compared to those for the cyclic octapeptides previously studied; ascidiacyclamide (1), patellamide D (2), cyclo(-Thr-D-Val(Thz)-Ile-)2 (3), and cyclo(-Thr-D-Val-αAbu-Ile-)2 (6). Both 4 and 5 contain two heterocyclic thiazole ring constraints but the latter has a larger degree of flexibility as a consequence of the glycine residues within the cyclic framework. The solution conformation of 4 and 5 was determined from 1H NMR spectra and found to be a “twisted figure of eight” similar to that for 2. Complexation studies using 1H NMR and CD spectroscopy yielded 1 ∶ 1 calcium–peptide binding constants (logK) for the two peptides (2.3 (4) and 5.7 (5)). For 5 the magnitude of the binding constant was verified by a competition titration using CD. The different calcium-binding affinities of 3 (logK = 4.0) and 4 is attributed to the stereochemistry of the threonine residue. The magnitude of the binding constant for 5 compared to 3 and 4 (all peptides containing two thiazole ring constrains) demonstrates that the increase in flexibility of the cyclic peptide has a dramatic effect on the Ca2+ binding ability. The affinity for Ca2+ thus decreases in the order (6 ∼ 5 > 3 > 2 ∼ 1 > 4). The number of carbonyl donors available on each peptide has only a limited effect on calcium binding. The most important factor is the flexibility, which allows for a conformation of the peptide capable of binding calcium efficiently." @default.
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• W1949089686 date "2002-02-11" @default.
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• W1949089686 title "Cyclic octapeptides containing thiazole. Effect of stereochemistry and degree of flexibility on calcium binding propertiesElectronic supplementary information (ESI) available: NOE and CD titration data for 5. See http://www.rsc.org/suppdata/p2/b1/b109168a/" @default.
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• W1949089686 doi "https://doi.org/10.1039/b109168a" @default.
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