Cystothiazole A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01132 |
| CAS | 207399-36-8 |
| Molecular Weight | 422.56 |
| Molecular Formula | C20H26N2O4S2 |
Online Inquiry
Description
It is produced by the strain of Cystobacter fuscus. It has antifungal activity. It can inhibit candida albicans, saccharomyces cerevisiae and aspergillus smoke with MIC of 0.4 μg/mL, 0.1 μg/mL and 1.6 μg/mL, respectively. It also inhibits human tumor cell, such as HPT-116 and K562 cells with MIC of 130 ng/mL and 110 ng/mL, respectively. It has no anti-bacterial effect.
Specification
| Synonyms | Melithiazole E; (+)-cystothiazole A; methyl (2E,4R,5S,6E)-3,5-dimethoxy-4-methyl-7-[2'-(propan-2-yl)-2,4'-bi-1,3-thiazol-4-yl]hepta-2,6-dienoate; (2E,6E)-(4R,5S)-7-(2'-Isopropyl-[2,4']bithiazolyl-4-yl)-3,5-dimethoxy-4-methyl-hepta-2,6-dienoic acid methyl ester |
| IUPAC Name | methyl (2E,4R,5S,6E)-3,5-dimethoxy-4-methyl-7-[2-(2-propan-2-yl-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]hepta-2,6-dienoate |
| Canonical SMILES | CC(C)C1=NC(=CS1)C2=NC(=CS2)C=CC(C(C)C(=CC(=O)OC)OC)OC |
| InChI | InChI=1S/C20H26N2O4S2/c1-12(2)19-22-15(11-28-19)20-21-14(10-27-20)7-8-16(24-4)13(3)17(25-5)9-18(23)26-6/h7-13,16H,1-6H3/b8-7+,17-9+/t13-,16+/m1/s1 |
| InChI Key | LRTJMINIVSPVMX-ZVJWTWILSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Fungi; Yeast |
| Melting Point | 111-112 °C |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Concise syntheses of cystothiazoles A, C, D, and melithiazol B
Yuki Iwaki, Hiroyuki Akita Chem Pharm Bull (Tokyo). 2007 Nov;55(11):1610-4. doi: 10.1248/cpb.55.1610.
A convergent synthesis of cystothiazoles C 1 and D 3 was achieved based on Julia coupling between the functionalized aldehyde 5b, corresponding to left half of the final molecule, and aryl sulfone 6 or 7, bearing a bithiazole moiety, corresponding to right half. Methylation of 1 and 3 gave cystothiazole A 2 and melithiazol B 4, respectively. The overall yield (5 steps from (2R,3S)-3-methylpent-4-yne-1,2-diol 10; 57%) of 5b via the present route was improved in comparison to that of the previously reported functionalized aldehyde 5a (7 steps from 10; 13%). By applying the modified Julia coupling method, selectivity (6E/6Z=20 : 1-26 : 1) toward the (6E)-form of the coupled products (15 or 19) against the corresponding (6Z)-form was improved in comparison to the Wittig method (6E/6Z=4 : 1-6.9 : 1).
2. Construction of a bacterial artificial chromosome library for a myxobacterium of the genus Cystobacter and characterization of an antibiotic biosynthetic gene cluster
Zhiyang Feng, Jianhua Qi, Takashi Tsuge, Yuichi Oba, Tetsuo Kobayashi, Yoshihiro Suzuki, Youji Sakagami, Makoto Ojika Biosci Biotechnol Biochem. 2005 Jul;69(7):1372-80. doi: 10.1271/bbb.69.1372.
A bacterial artificial chromosome (BAC) library was constructed to isolate the biosynthetic gene cluster for the polyketide/peptide hybrid-type antibiotic cystothiazole A from the myxobacterium Cystobacter fuscus strain AJ-13278. Sequence analysis of a 63.9 kb contiguous region that encompasses the biosynthetic gene cluster (cta) led to the identification of a polyketide synthase (PKS)/nonribosomal peptide synthetase (NRPS) hybrid gene cluster 32.1 kb in size, which consists of six open reading frames (ORFs), ctaB to ctaG, as well as downstream genes ctaJ and ctaK (1.0 and 0.9 kb, respectively) responsible for the final biosynthetic steps. The genes ctaB, ctaE, and ctaF encode PKSs, the genes ctaC and ctaG encode NRPSs, and ctaD encodes an NRPS-PKS hybrid enzyme. Disruption of ctaD impaired cystothiazole A production. Additionally, two downstream genes, ctaJ and ctaK, which encode a nitrilase and an O-methyltransferase, respectively, must be responsible for the final methyl ester formation in the cystothiazole A biosynthesis.
3. Highly enantio- and diastereoselective vinylogous aldol reaction by LiCl-assisted BINOL-titanium species
Guowei Wang, Baomin Wang, Shuai Qi, Jinfeng Zhao, Yuhan Zhou, Jingping Qu Org Lett. 2012 Jun 1;14(11):2734-7. doi: 10.1021/ol300946j. Epub 2012 May 23.
The first highly enantio- and diastereoselective vinylogous aldol reaction between propionyl acetate-derived Brassard's diene and aldehydes was accomplished by titanium-lithium combined Lewis acid, affording δ-hydroxy-γ-methyl-β-methoxy acrylates. This methodology was utilized in convenient and concise construction of the polypropionate moiety in cystothiazole A and melithiazole C.
Recommended Products
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
