Caprazamycin
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| Category | Antibiotics |
| Catalog number | BBF-00215 |
| CAS | 327164-11-4 |
| Molecular Weight | 1146.28 |
| Molecular Formula | C53H87N5O22 |
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Description
Caprazamycin is a liponucleoside antibiotic isolated from Streptomyces sp. MK730-62F2.
Specification
| IUPAC Name | 2-[[(2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxyoxolan-2-yl]oxy-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-1,4-dimethyl-6-[14-methyl-3-[3-methyl-5-oxo-5-(3,4,5-trimethoxy-6-methyloxan-2-yl)oxypentanoyl]oxypentadecanoyl]oxy-3-oxo-1,4-diazepane-5-carboxylic acid |
| Canonical SMILES | CC1C(C(C(C(O1)OC(=O)CC(C)CC(=O)OC(CCCCCCCCCCC(C)C)CC(=O)OC2CN(C(C(=O)N(C2C(=O)O)C)C(C3C(C(C(O3)N4C=CC(=O)NC4=O)O)O)OC5C(C(C(O5)CN)O)O)C)OC)OC)OC |
| InChI | InChI=1S/C53H87N5O22/c1-27(2)18-16-14-12-10-11-13-15-17-19-30(75-34(60)22-28(3)23-35(61)78-52-47(73-9)46(72-8)43(71-7)29(4)74-52)24-36(62)76-32-26-56(5)38(48(67)57(6)37(32)50(68)69)44(80-51-42(66)39(63)31(25-54)77-51)45-40(64)41(65)49(79-45)58-21-20-33(59)55-53(58)70/h20-21,27-32,37-47,49,51-52,63-66H,10-19,22-26,54H2,1-9H3,(H,68,69)(H,55,59,70)/t28?,29?,30?,31-,32?,37?,38?,39-,40+,41-,42-,43?,44?,45+,46?,47?,49-,51+,52?/m1/s1 |
| InChI Key | IDKBSYZJTHLMLI-MHDDYUJTSA-N |
Properties
| Antibiotic Activity Spectrum | mycobacteria |
Reference Reading
1. Synthesis of isoxazolidine-containing uridine derivatives as caprazamycin analogues
Satoshi Ichikawa, Mayumi Yamaguchi, Akira Matsuda Org Biomol Chem . 2015 Jan 28;13(4):1187-97. doi: 10.1039/c4ob02142h.
Simplification of caprazamycins, which are promising antibacterial nucleoside natural products, was conducted by scaffold-hopping of the structurally complex diazepanone moiety to the isoxazolidine scaffold. The designed isoxazolidine-containing uridine derivatives were synthesized by an intramolecular 1,3-dipolar cycloaddition of alkenyl nitrone as a key step. The lactone-fused isoxazolidine intermediate was easily converted to the target compounds by sequential introduction of key substituents upon ring-opening the lactone moiety by nucleophilic substitution and electrophilic capping of the resulting primary alcohol. Several analogues exhibited good activity against H. influenzae ATCC 10211 (MIC 0.25-0.5 μg mL(-1)) and moderate activity against vancomycin-resistant E. faecalis SR7914 (MIC 4-8 μg mL(-1)).
2. Total Synthesis of Caprazamycin A: Practical and Scalable Synthesis of syn-β-Hydroxyamino Acids and Introduction of a Fatty Acid Side Chain to 1,4-Diazepanone
Shinsuke Yokouchi, Yoshiji Takemoto, Yusuke Kobayashi, Hugh Nakamura, Takuma Yoshida, Masayuki Igarashi, Motohiro Yasui, Chihiro Tsukano J Am Chem Soc . 2019 May 29;141(21):8527-8540. doi: 10.1021/jacs.9b02220.
The first total synthesis of caprazamycin A (1), a representative liponucleoside antibiotic, is described. Diastereoselective aldol reactions of aldehydes 12 and 25-27, derived from uridine, with diethyl isocyanomalonate 13 and phenylcarbamate 21 were investigated using thiourea catalysts 14 or bases to synthesize syn-β-hydroxyamino acid derivatives. The 1,4-diazepanone core of 1 was constructed using a Mitsunobu reaction, and the fatty acid side chain was introduced using a stepwise sequence based on model studies. Notably, global deprotection was realized using palladium black and formic acid without hydrogenating the olefin in the uridine unit.
3. Identification and manipulation of the caprazamycin gene cluster lead to new simplified liponucleoside antibiotics and give insights into the biosynthetic pathway
Bernd Kammerer, Bertolt Gust, Emmanuel Wemakor, Liane Lutsch, Stefanie Siebenberg, Leonard Kaysser J Biol Chem . 2009 May 29;284(22):14987-96. doi: 10.1074/jbc.M901258200.
Caprazamycins are potent anti-mycobacterial liponucleoside antibiotics isolated from Streptomyces sp. MK730-62F2 and belong to the translocase I inhibitor family. Their complex structure is derived from 5'-(beta-O-aminoribosyl)-glycyluridine and comprises a unique N-methyldiazepanone ring. The biosynthetic gene cluster has been identified, cloned, and sequenced, representing the first gene cluster of a translocase I inhibitor. Sequence analysis revealed the presence of 23 open reading frames putatively involved in export, resistance, regulation, and biosynthesis of the caprazamycins. Heterologous expression of the gene cluster in Streptomyces coelicolor M512 led to the production of non-glycosylated bioactive caprazamycin derivatives. A set of gene deletions validated the boundaries of the cluster and inactivation of cpz21 resulted in the accumulation of novel simplified liponucleoside antibiotics that lack the 3-methylglutaryl moiety. Therefore, Cpz21 is assigned to act as an acyltransferase in caprazamycin biosynthesis. In vivo and in silico analysis of the caprazamycin biosynthetic gene cluster allows a first proposal of the biosynthetic pathway and provides insights into the biosynthesis of related uridyl-antibiotics.
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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 ╳
