Carbomycin

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

MedKoo CAT#: 592193

CAS#: 4564-87-8

Description: Carbomycin has activity against Borrelia burgdorferi persisters (lyme disease).


Chemical Structure

img
Carbomycin
CAS# 4564-87-8

Theoretical Analysis

MedKoo Cat#: 592193
Name: Carbomycin
CAS#: 4564-87-8
Chemical Formula: C42H67NO16
Exact Mass: 841.446
Molecular Weight: 841.99
Elemental Analysis: C, 59.91; H, 8.02; N, 1.66; O, 30.40

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 @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Carbomycin

IUPAC/Chemical Name: (2S,3S,4R,6S)-6-(((2R,3S,4R,5R,6S)-6-(((1S,3R,7R,8S,9S,10R,12R,16S,E)-7-acetoxy-8-methoxy-3,12-dimethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-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 Key: FQVHOULQCKDUCY-OGHXVOSASA-N

InChi Code: InChI=1S/C42H67NO16/c1-21(2)16-32(47)57-40-25(6)53-34(20-42(40,8)50)58-37-24(5)54-41(36(49)35(37)43(9)10)59-38-27(14-15-44)17-22(3)28(46)12-13-29-30(56-29)18-23(4)52-33(48)19-31(39(38)51-11)55-26(7)45/h12-13,15,21-25,27,29-31,34-41,49-50H,14,16-20H2,1-11H3/b13-12+/t22-,23-,24-,25+,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1

SMILES Code: CO[C@H]1[C@H](OC(C)=O)CC(O[C@@H](C[C@@H]2O[C@H]2/C=C/C([C@@H](C[C@@H]([C@@H]1O[C@@H]3O[C@@H]([C@H]([C@H](N(C)C)[C@H]3O)O[C@H]4C[C@@](O)([C@H]([C@@H](O4)C)OC(CC(C)C)=O)C)C)CC=O)C)=O)C)=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 841.99 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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Niu H, Yee R, Cui P, Tian L, Zhang S, Shi W, Sullivan D, Zhu B, Zhang W, Zhang Y. Identification of Agents Active against Methicillin-Resistant Staphylococcus aureus USA300 from a Clinical Compound Library. Pathogens. 2017 Sep 20;6(3). pii: E44. doi: 10.3390/pathogens6030044. PubMed PMID: 28930155; PubMed Central PMCID: PMC5618001.

2: Zhong J, Lu Z, Dai J, He W. Identification of two regulatory genes involved in carbomycin biosynthesis in Streptomyces thermotolerans. Arch Microbiol. 2017 Sep;199(7):1023-1033. doi: 10.1007/s00203-017-1376-z. Epub 2017 Apr 7. PubMed PMID: 28389815.

3: 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.

4: Li ZL, Wang YH, Chu J, Zhuang YP, Zhang SL. Leucine improves the component of isovalerylspiramycins for the production of bitespiramycin. Bioprocess Biosyst Eng. 2009 Aug;32(5):641-7. doi: 10.1007/s00449-008-0287-4. Epub 2008 Dec 30. PubMed PMID: 19115067.

5: Wu LZ, Ma CY, Wang YG, Dai JL, Li JY, Xia HZ. [Deletion of spiramycin 3-O-acyltransferase gene from Streptomyces spiramyceticus F21 resulting in the production of spiramycin I as major component]. Sheng Wu Gong Cheng Xue Bao. 2007 Jul;23(4):612-7. Chinese. PubMed PMID: 17849607.

6: Lovmar M, Tenson T, Ehrenberg M. Kinetics of macrolide action: the josamycin and erythromycin cases. J Biol Chem. 2004 Dec 17;279(51):53506-15. Epub 2004 Sep 22. PubMed PMID: 15385552.

7: Liu M, Douthwaite S. Resistance to the macrolide antibiotic tylosin is conferred by single methylations at 23S rRNA nucleotides G748 and A2058 acting in synergy. Proc Natl Acad Sci U S A. 2002 Nov 12;99(23):14658-63. Epub 2002 Nov 4. PubMed PMID: 12417742; PubMed Central PMCID: PMC137475.

8: Hansen JL, Ippolito JA, Ban N, Nissen P, Moore PB, Steitz TA. The structures of four macrolide antibiotics bound to the large ribosomal subunit. Mol Cell. 2002 Jul;10(1):117-28. PubMed PMID: 12150912.

9: Poulsen SM, Karlsson M, Johansson LB, Vester B. The pleuromutilin drugs tiamulin and valnemulin bind to the RNA at the peptidyl transferase centre on the ribosome. Mol Microbiol. 2001 Sep;41(5):1091-9. PubMed PMID: 11555289.

10: Shenin IuD, Novikova II, Kaminskiĭ GV, Ivanova IA. [Alirinomycin C--a novel macrolide antibiotic from Streptomyces felleus VIZR 8]. Antibiot Khimioter. 2001;46(2):10-6. Russian. PubMed PMID: 11544745.

11: 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.

12: Anadón A, Reeve-johnson L. Macrolide antibiotics, drug interactions and microsomal enzymes: implications for veterinary medicine. Res Vet Sci. 1999 Jun;66(3):197-203. Review. PubMed PMID: 10333459.

13: Christner C, Küllertz G, Fischer G, Zerlin M, Grabley S, Thiericke R, Taddei A, Zeeck A. Albocycline- and carbomycin-type macrolides, inhibitors of human prolyl endopeptidases. J Antibiot (Tokyo). 1998 Mar;51(3):368-71. PubMed PMID: 9589074.

14: Nitta I, Ueda T, Watanabe K. Possible involvement of Escherichia coli 23S ribosomal RNA in peptide bond formation. RNA. 1998 Mar;4(3):257-67. Retraction in: Nitta I, Ueda T, Watanabe K. RNA. 1999 May;5(5):707. PubMed PMID: 9510328; PubMed Central PMCID: PMC1369615.

15: 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.

16: Aagaard C, Leviev I, Aravalli RN, Forterre P, Prieur D, Garrett RA. General vectors for archaeal hyperthermophiles: strategies based on a mobile intron and a plasmid. FEMS Microbiol Rev. 1996 May;18(2-3):93-104. Review. PubMed PMID: 8639332.

17: 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.

18: Rodriguez-Fonseca C, Amils R, Garrett RA. Fine structure of the peptidyl transferase centre on 23 S-like rRNAs deduced from chemical probing of antibiotic-ribosome complexes. J Mol Biol. 1995 Mar 24;247(2):224-35. PubMed PMID: 7707371.

19: Aagaard C, Phan H, Trevisanato S, Garrett RA. A spontaneous point mutation in the single 23S rRNA gene of the thermophilic arachaeon Sulfolobus acidocaldarius confers multiple drug resistance. J Bacteriol. 1994 Dec;176(24):7744-7. PubMed PMID: 8002603; PubMed Central PMCID: PMC197236.

20: Arisawa A, Kawamura N, Takeda K, Tsunekawa H, Okamura K, Okamoto R. Cloning of the macrolide antibiotic biosynthesis gene acyA, which encodes 3-O-acyltransferase, from Streptomyces thermotolerans and its use for direct fermentative production of a hybrid macrolide antibiotic. Appl Environ Microbiol. 1994 Jul;60(7):2657-60. PubMed PMID: 8074537; PubMed Central PMCID: PMC201700.