Carbomycin B

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

MedKoo CAT#: 598660

CAS#: 21238-30-2

Description: Carbomycin B is an intermediate in the synthesis of Carbomycin, a macrolite antibiotic complex similar to Leucomycin and Erythromycin, produced by Stroptomyces halstedii.

Chemical Structure

Carbomycin B
CAS# 21238-30-2

Theoretical Analysis

MedKoo Cat#: 598660
Name: Carbomycin B
CAS#: 21238-30-2
Chemical Formula: C42H67NO15
Exact Mass: 825.4511
Molecular Weight: 825.99
Elemental Analysis: C, 61.07; H, 8.18; N, 1.70; O, 29.05

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Carbomycin B; Magnamycin B;

IUPAC/Chemical Name: (2S,3S,4R,6S)-6-(((2R,3S,4R,5R,6S)-6-(((4R,5S,6S,7R,9R,11E,13E,16R)-4-acetoxy-5-methoxy-9,16-dimethyl-2,10-dioxo-7-(2-oxoethyl)oxacyclohexadeca-11,13-dien-6-yl)oxy)-4-(dimethylamino)-5-hydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-4-hydroxy-2,4-dimethyltetrahydro-2H-pyran-3-yl 3-methylbutanoate


InChi Code: InChI=1S/C42H67NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29,31,34-41,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1

SMILES Code: C[C@@H]1C/C=C/C=C/C([C@H](C)C[C@H](CC=O)[C@H](O[C@H]2[C@H](O)[C@@H](N(C)C)[C@H](O[C@H]3C[C@@](C)(O)[C@@H](OC(CC(C)C)=O)[C@H](C)O3)[C@@H](C)O2)[C@@H](OC)[C@H](OC(C)=O)CC(O1)=O)=O

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

Preparing Stock Solutions

The following data is based on the product molecular weight 825.99 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

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1: BRANNICK TL, HEILMAN FR, NICHOLS DR, MARTIN WJ. Comparison of levels of carbomycin A, carbomycin B, and erythromycin in serum and thyroid tissue. Antibiotic Med Clin Ther (New York). 1955 Mar;1(3):131-5. PubMed PMID: 14362447.

2: Moazed D, Noller HF. Chloramphenicol, erythromycin, carbomycin and vernamycin B protect overlapping sites in the peptidyl transferase region of 23S ribosomal RNA. Biochimie. 1987 Aug;69(8):879-84. PubMed PMID: 3122849.

3: FAIRBROTHER RW, JENNINGS RC. The dried disc technique with bacitracin, carbomycin, erythromycin, polymyxin B, and tetracycline. J Clin Pathol. 1955 May;8(2):117-9. PubMed PMID: 14367541; PubMed Central PMCID: PMC1023767.

4: Arisawa A, Tsunekawa H, Okamura K, Okamoto R. Nucleotide sequence analysis of the carbomycin biosynthetic genes including the 3-O-acyltransferase gene from Streptomyces thermotolerans. Biosci Biotechnol Biochem. 1995 Apr;59(4):582-8. PubMed PMID: 7772821.

5: Tatsuta K, Tanaka A, Fujimoto K, Kinoshita M, Umezawa S. Synthesis of carbomycin B. Introduction of the amino disaccharide onto the 16-membered-ring aglycone. J Am Chem Soc. 1977 Aug 17;99(17):5826-7. PubMed PMID: 886125.

6: BARDIER A, COMBES B, DEGOY A, MONNIER J. [Blood and urinary concentrations of carbomycin B after oral administration in infants]. Toulouse Med. 1956 Jul;57(7):569-78. French. PubMed PMID: 13371616.

7: Poulsen SM, Kofoed C, Vester B. Inhibition of the ribosomal peptidyl transferase reaction by the mycarose moiety of the antibiotics carbomycin, spiramycin and tylosin. J Mol Biol. 2000 Dec 1;304(3):471-81. PubMed PMID: 11090288.

8: Epp JK, Burgett SG, Schoner BE. Cloning and nucleotide sequence of a carbomycin-resistance gene from Streptomyces thermotolerans. Gene. 1987;53(1):73-83. PubMed PMID: 3036668.

9: Feng J, Wang T, Shi W, Zhang S, Sullivan D, Auwaerter PG, Zhang Y. Identification of novel activity against Borrelia burgdorferi persisters using an FDA approved drug library. Emerg Microbes Infect. 2014 Jul;3(7):e49. doi: 10.1038/emi.2014.53. Epub 2014 Jul 2. PubMed PMID: 26038747; PubMed Central PMCID: PMC4126181.

10: HANF U. [Studies of the sensitivity in vitro of Actinomyces israeli to erythromycin, magnamycin, polymyxin B, bacitracin, neomycin, tyrothricin, xanthocillin and suprathricin]. Z Hyg Infektionskr. 1956;143(2):127-33. German. PubMed PMID: 13401963.

11: Birmingham VA, Cox KL, Larson JL, Fishman SE, Hershberger CL, Seno ET. Cloning and expression of a tylosin resistance gene from a tylosin-producing strain of Streptomyces fradiae. Mol Gen Genet. 1986 Sep;204(3):532-9. PubMed PMID: 3020383.

12: Kamimiya S, Weisblum B. Induction of ermSV by 16-membered-ring macrolide antibiotics. Antimicrob Agents Chemother. 1997 Mar;41(3):530-4. PubMed PMID: 9055987; PubMed Central PMCID: PMC163745.

13: Kondo K. Analytical studies of maridomycin. I. High-performance liquid chromatography of marido-mycins and some other macrolide antibiotics. J Chromatogr. 1979 Feb 1;169:329-36. PubMed PMID: 536423.

14: Mitchell CH, England JM, Attardi G. Isolation of chloramphenicol-resistant variants from a human cell line. Somatic Cell Genet. 1975 Jul;1(3):215-34. PubMed PMID: 800292.

15: Pestka S. Antibiotics as probes of ribosome structure: binding of chloramphenicol and erythromycin to polyribosomes; effect of other antibiotics. Antimicrob Agents Chemother. 1974 Mar;5(3):255-67. PubMed PMID: 4599122; PubMed Central PMCID: PMC428957.

16: Jones RH, Bennett FW. Bacteriophage types and antibiotic sensitivity of staphylococci from bovine milk and human nares. Appl Microbiol. 1965 Sep;13(5):725-31. PubMed PMID: 5325936; PubMed Central PMCID: PMC1058332.