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MedKoo Cat#: 461444 | Name: Clorobiocin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Clorobiocin is an aminocoumarin antibacterial that inhibits the enzyme DNA gyrase.

Chemical Structure

Clorobiocin
Clorobiocin
CAS#39868-96-7

Theoretical Analysis

MedKoo Cat#: 461444

Name: Clorobiocin

CAS#: 39868-96-7

Chemical Formula: C35H37ClN2O11

Exact Mass: 696.2086

Molecular Weight: 697.13

Elemental Analysis: C, 60.30; H, 5.35; Cl, 5.09; N, 4.02; O, 25.24

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Clorobiocin; RP 18631; RP-18631; RP18631;
IUPAC/Chemical Name
(3R,4S,5R,6S)-6-((8-chloro-4-hydroxy-3-(4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamido)-2-oxo-2H-chromen-7-yl)oxy)-5-hydroxy-3-methoxy-2,2-dimethyltetrahydro-2H-pyran-4-yl 5-methyl-1H-pyrrole-2-carboxylate
InChi Key
FJAQNRBDVKIIKK-LFLQOBSNSA-N
InChi Code
InChI=1S/C35H37ClN2O11/c1-16(2)7-9-18-15-19(10-13-22(18)39)31(42)38-25-26(40)20-11-14-23(24(36)28(20)47-33(25)44)46-34-27(41)29(30(45-6)35(4,5)49-34)48-32(43)21-12-8-17(3)37-21/h7-8,10-15,27,29-30,34,37,39-41H,9H2,1-6H3,(H,38,42)/t27-,29+,30-,34-/m1/s1
SMILES Code
O=C(C1=CC=C(C)N1)O[C@@H]2[C@@H](OC)C(C)(C)O[C@@H](OC3=C(Cl)C(O4)=C(C=C3)C(O)=C(NC(C5=CC=C(O)C(C/C=C(C)\C)=C5)=O)C4=O)[C@@H]2O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 697.13 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Rückert C, Kalinowski J, Heide L, Apel AK. Draft Genome Sequence of Streptomyces roseochromogenes subsp. oscitans DS 12.976, Producer of the Aminocoumarin Antibiotic Clorobiocin. Genome Announc. 2014 Jan 9;2(1). pii: e01147-13. doi: 10.1128/genomeA.01147-13. PubMed PMID: 24407645; PubMed Central PMCID: PMC3886958. 2: Flinspach K, Westrich L, Kaysser L, Siebenberg S, Gomez-Escribano JP, Bibb M, Gust B, Heide L. Heterologous expression of the biosynthetic gene clusters of coumermycin A(1), clorobiocin and caprazamycins in genetically modified Streptomyces coelicolor strains. Biopolymers. 2010 Sep;93(9):823-32. doi: 10.1002/bip.21493. PubMed PMID: 20578003. 3: Eustáquio AS, Gust B, Luft T, Li SM, Chater KF, Heide L. Clorobiocin biosynthesis in Streptomyces: identification of the halogenase and generation of structural analogs. Chem Biol. 2003 Mar;10(3):279-88. PubMed PMID: 12670542. 4: Freitag A, Wemakor E, Li SM, Heide L. Acyl transfer in clorobiocin biosynthesis: involvement of several proteins in the transfer of the pyrrole-2-carboxyl moiety to the deoxysugar. Chembiochem. 2005 Dec;6(12):2316-25. PubMed PMID: 16276503. 5: Wolpert M, Gust B, Kammerer B, Heide L. Effects of deletions of mbtH-like genes on clorobiocin biosynthesis in Streptomyces coelicolor. Microbiology. 2007 May;153(Pt 5):1413-23. PubMed PMID: 17464055. 6: Pojer F, Li SM, Heide L. Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster: new insights into the biosynthesis of aminocoumarin antibiotics. Microbiology. 2002 Dec;148(Pt 12):3901-11. PubMed PMID: 12480894. 7: Xu H, Kahlich R, Kammerer B, Heide L, Li SM. CloN2, a novel acyltransferase involved in the attachment of the pyrrole-2-carboxyl moiety to the deoxysugar of clorobiocin. Microbiology. 2003 Aug;149(Pt 8):2183-91. PubMed PMID: 12904558. 8: Westrich L, Heide L, Li SM. CloN6, a novel methyltransferase catalysing the methylation of the pyrrole-2-carboxyl moiety of clorobiocin. Chembiochem. 2003 Aug 4;4(8):768-73. PubMed PMID: 12898629. 9: Galm U, Heller S, Shapiro S, Page M, Li SM, Heide L. Antimicrobial and DNA gyrase-inhibitory activities of novel clorobiocin derivatives produced by mutasynthesis. Antimicrob Agents Chemother. 2004 Apr;48(4):1307-12. PubMed PMID: 15047534; PubMed Central PMCID: PMC375324. 10: Anderle C, Alt S, Gulder T, Bringmann G, Kammerer B, Gust B, Heide L. Biosynthesis of clorobiocin: investigation of the transfer and methylation of the pyrrolyl-2-carboxyl moiety. Arch Microbiol. 2007 Mar;187(3):227-37. Epub 2006 Nov 25. PubMed PMID: 17308937. 11: Pojer F, Kahlich R, Kammerer B, Li SM, Heide L. CloR, a bifunctional non-heme iron oxygenase involved in clorobiocin biosynthesis. J Biol Chem. 2003 Aug 15;278(33):30661-8. Epub 2003 May 30. PubMed PMID: 12777382. 12: Metzger U, Keller S, Stevenson CE, Heide L, Lawson DM. Structure and mechanism of the magnesium-independent aromatic prenyltransferase CloQ from the clorobiocin biosynthetic pathway. J Mol Biol. 2010 Dec 10;404(4):611-26. doi: 10.1016/j.jmb.2010.09.067. Epub 2010 Oct 12. PubMed PMID: 20946900. 13: Cejka K, Holubová I, Hubácek J. Curing effect of clorobiocin on Escherichia coli plasmids. Mol Gen Genet. 1982;186(1):153-5. PubMed PMID: 7050623. 14: Freitag A, Galm U, Li SM, Heide L. New aminocoumarin antibiotics from a cloQ-defective mutant of the clorobiocin producer Streptomyces roseochromogenes DS12.976. J Antibiot (Tokyo). 2004 Mar;57(3):205-9. PubMed PMID: 15152806. 15: Freitag A, Méndez C, Salas JA, Kammerer B, Li SM, Heide L. Metabolic engineering of the heterologous production of clorobiocin derivatives and elloramycin in Streptomyces coelicolor M512. Metab Eng. 2006 Nov;8(6):653-61. Epub 2006 Aug 4. PubMed PMID: 16996763. 16: Pojer F, Wemakor E, Kammerer B, Chen H, Walsh CT, Li SM, Heide L. CloQ, a prenyltransferase involved in clorobiocin biosynthesis. Proc Natl Acad Sci U S A. 2003 Mar 4;100(5):2316-21. PubMed PMID: 12618544; PubMed Central PMCID: PMC151338. 17: Eustáquio AS, Gust B, Galm U, Li SM, Chater KF, Heide L. Heterologous expression of novobiocin and clorobiocin biosynthetic gene clusters. Appl Environ Microbiol. 2005 May;71(5):2452-9. PubMed PMID: 15870333; PubMed Central PMCID: PMC1087579. 18: Hooper DC, Wolfson JS, McHugh GL, Winters MB, Swartz MN. Effects of novobiocin, coumermycin A1, clorobiocin, and their analogs on Escherichia coli DNA gyrase and bacterial growth. Antimicrob Agents Chemother. 1982 Oct;22(4):662-71. PubMed PMID: 6295263; PubMed Central PMCID: PMC183811. 19: Anderle C, Li SM, Kammerer B, Gust B, Heide L. New aminocoumarin antibiotics derived from 4-hydroxycinnamic acid are formed after heterologous expression of a modified clorobiocin biosynthetic gene cluster. J Antibiot (Tokyo). 2007 Aug;60(8):504-10. PubMed PMID: 17827661. 20: Garneau S, Dorrestein PC, Kelleher NL, Walsh CT. Characterization of the formation of the pyrrole moiety during clorobiocin and coumermycin A1 biosynthesis. Biochemistry. 2005 Mar 1;44(8):2770-80. PubMed PMID: 15723521.