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Cyclothialidine C

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Category Enzyme inhibitors
Catalog number BBF-01120
CAS 161161-54-2
Molecular Weight 625.66
Molecular Formula C26H35N5O11S

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is produced by the strain of Streptomyces sp. NR 0659. It and its homologues inhibit escherichia coli DNA helicases with IC50 of 0.7 μmol/L, and the reference neomycin was 1.2 μmol/L.

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IUPAC Name (2S)-2-[[(5S,8S)-8-[[(2S,3R)-1-[(2S)-2-aminopropanoyl]-3-hydroxypyrrolidine-2-carbonyl]amino]-14,16-dihydroxy-13-methyl-7,11-dioxo-10-oxa-3-thia-6-azabicyclo[10.4.0]hexadeca-1(16),12,14-triene-5-carbonyl]amino]propanoic acid
Canonical SMILES CC1=C2C(=C(C=C1O)O)CSCC(NC(=O)C(COC2=O)NC(=O)C3C(CCN3C(=O)C(C)N)O)C(=O)NC(C)C(=O)O
InChI InChI=1S/C26H35N5O11S/c1-10-17(33)6-18(34)13-8-43-9-15(22(36)28-12(3)25(39)40)30-21(35)14(7-42-26(41)19(10)13)29-23(37)20-16(32)4-5-31(20)24(38)11(2)27/h6,11-12,14-16,20,32-34H,4-5,7-9,27H2,1-3H3,(H,28,36)(H,29,37)(H,30,35)(H,39,40)/t11-,12-,14-,15+,16+,20-/m0/s1
InChI Key FSQBBUCGXSRLHM-XWKXLRLCSA-N
Solubility Soluble in Water, Methanol
1. Crystallization of inhibitor complexes of an N-terminal 24 kDa fragment of the DNA gyrase B protein
R J Lewis, O M Singh, C V Smith, A Maxwell, T Skarzynski, A J Wonacott, D B Wigley J Mol Biol. 1994 Aug 5;241(1):128-30. doi: 10.1006/jmbi.1994.1480.
A 24 kDa N-terminal fragment of the Escherichia coli DNA gyrase B protein has been crystallized in the presence of novobiocin. One crystal form has been obtained that is orthorhombic, P2(1)2(1)2(1), with unit cell dimensions a = 40.3 A, b = 47.7 A, c = 111.9 A. The asymmetric unit of this crystal form contains one molecule (Vm = 2.24 A3/Da). Complete native data have been collected to 2.5 A resolution. This same protein fragment has also been crystallized in the presence of GR122222X, an inhibitor that is structurally related to cyclothialidine. These crystals also exhibit P2(1)2(1)2(1) symmetry but have unit cell dimensions of a = 68.8 A, b = 68.6 A, c = 48.6 A. The Vm value of this crystal form is 2.39 A3/Da, assuming one molecule in the asymmetric unit, and native data have been collected to 2.0 A resolution. Molecular replacement studies of both complexes are underway.
2. Cyclothialidine analogs, novel DNA gyrase inhibitors
K Yamaji, M Masubuchi, F Kawahara, Y Nakamura, A Nishio, S Matsukuma, M Fujimori, N Nakada, J Watanabe, T Kamiyama J Antibiot (Tokyo). 1997 May;50(5):402-11. doi: 10.7164/antibiotics.50.402.
DNA gyrase inhibitors, cyclothialidines B, C, D and E were isolated from four Streptomycete strains (NR 0659, NR 0660, NR 0661 and NR 0662). Their structures have been elucidated based on the amino acid analysis of the hydrolysates, NMR and HRFAB-MS experiments and shown to be cyclothialidine analogs. The absolute stereochemistry has been determined by the chiral HPLC analysis of the hydrolysates. Cyclothialidines B, D and E are novel and potent inhibitors of DNA gyrase.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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