MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 412288 | Name: Capuramycin

Description:

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

Capuramycin is a biochemical with antibacterial activity

Chemical Structure

Capuramycin
Capuramycin
CAS#102770-00-3

Theoretical Analysis

MedKoo Cat#: 412288

Name: Capuramycin

CAS#: 102770-00-3

Chemical Formula: C23H31N5O12

Exact Mass: 569.1969

Molecular Weight: 569.52

Elemental Analysis: C, 48.51; H, 5.49; N, 12.30; O, 33.71

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Capuramycin;
IUPAC/Chemical Name
(2S,3S,4S)-2-((R)-2-amino-1-((2S,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-3-methoxytetrahydrofuran-2-yl)-2-oxoethoxy)-3,4-dihydroxy-N-((S)-2-oxoazepan-3-yl)-3,4-dihydro-2H-pyran-6-carboxamide
InChi Key
BISOEENGZHMDEO-RLXIHFJVSA-N
InChi Code
InChI=1S/C23H31N5O12/c1-37-15-14(32)21(28-7-5-12(30)27-23(28)36)39-16(15)17(18(24)33)40-22-13(31)10(29)8-11(38-22)20(35)26-9-4-2-3-6-25-19(9)34/h5,7-10,13-17,21-22,29,31-32H,2-4,6H2,1H3,(H2,24,33)(H,25,34)(H,26,35)(H,27,30,36)/t9-,10-,13-,14+,15-,16-,17+,21+,22+/m0/s1
SMILES Code
CO[C@H]1[C@H]([C@H](N2C=CC(NC2=O)=O)O[C@@H]1[C@H](C(N)=O)O[C@H]3OC(C(N[C@H]4CCCCNC4=O)=O)=C[C@@H]([C@@H]3O)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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 569.52 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: Mitachi K, Kansal RG, Hevener KE, Gillman CD, Hussain SM, Yun HG, Miranda- Carboni GA, Glazer ES, Clemons WM Jr, Kurosu M. DPAGT1 Inhibitors of Capuramycin Analogues and Their Antimigratory Activities of Solid Tumors. J Med Chem. 2020 Oct 8;63(19):10855-10878. doi: 10.1021/acs.jmedchem.0c00545. Epub 2020 Sep 18. PMID: 32886511; PMCID: PMC7554145. 2: Bugg TDH, Kerr RV. Mechanism of action of nucleoside antibacterial natural product antibiotics. J Antibiot (Tokyo). 2019 Dec;72(12):865-876. doi: 10.1038/s41429-019-0227-3. Epub 2019 Aug 30. PMID: 31471595. 3: Mashalidis EH, Kaeser B, Terasawa Y, Katsuyama A, Kwon DY, Lee K, Hong J, Ichikawa S, Lee SY. Chemical logic of MraY inhibition by antibacterial nucleoside natural products. Nat Commun. 2019 Jul 2;10(1):2917. doi: 10.1038/s41467-019-10957-9. PMID: 31266949; PMCID: PMC6606608. 4: Biecker AL, Liu X, Thorson JS, Yang Z, Van Lanen SG. Biosynthetic and Synthetic Strategies for Assembling Capuramycin-Type Antituberculosis Antibiotics. Molecules. 2019 Jan 25;24(3):433. doi: 10.3390/molecules24030433. PMID: 30691073; PMCID: PMC6384614. 5: Huang Y, Liu X, Cui Z, Wiegmann D, Niro G, Ducho C, Song Y, Yang Z, Van Lanen SG. Pyridoxal-5'-phosphate as an oxygenase cofactor: Discovery of a carboxamide- forming, α-amino acid monooxygenase-decarboxylase. Proc Natl Acad Sci U S A. 2018 Jan 30;115(5):974-979. doi: 10.1073/pnas.1718667115. Epub 2018 Jan 17. PMID: 29343643; PMCID: PMC5798378. 6: Liu X, Jin Y, Cai W, Green KD, Goswami A, Garneau-Tsodikova S, Nonaka K, Baba S, Funabashi M, Yang Z, Van Lanen SG. A biocatalytic approach to capuramycin analogues by exploiting a substrate permissive N-transacylase CapW. Org Biomol Chem. 2016 Apr 28;14(16):3956-62. doi: 10.1039/c6ob00381h. Epub 2016 Apr 6. PMID: 27050157; PMCID: PMC4864588. 7: Liu X, Jin Y, Cui Z, Nonaka K, Baba S, Funabashi M, Yang Z, Van Lanen SG. The Role of a Nonribosomal Peptide Synthetase in l-Lysine Lactamization During Capuramycin Biosynthesis. Chembiochem. 2016 May 3;17(9):804-10. doi: 10.1002/cbic.201500701. Epub 2016 Mar 18. PMID: 26840634; PMCID: PMC4933962. 8: Moore JH 2nd, van Opstal E, Kolling GL, Shin JH, Bogatcheva E, Nikonenko B, Einck L, Phipps AJ, Guerrant RL, Protopopova M, Warren CA. Treatment of Clostridium difficile infection using SQ641, a capuramycin analogue, increases post-treatment survival and improves clinical measures of disease in a murine model. J Antimicrob Chemother. 2016 May;71(5):1300-6. doi: 10.1093/jac/dkv479. Epub 2016 Jan 31. PMID: 26832756; PMCID: PMC4830414. 9: Cai W, Goswami A, Yang Z, Liu X, Green KD, Barnard-Britson S, Baba S, Funabashi M, Nonaka K, Sunkara M, Morris AJ, Spork AP, Ducho C, Garneau- Tsodikova S, Thorson JS, Van Lanen SG. The Biosynthesis of Capuramycin-type Antibiotics: IDENTIFICATION OF THE A-102395 BIOSYNTHETIC GENE CLUSTER, MECHANISM OF SELF-RESISTANCE, AND FORMATION OF URIDINE-5'-CARBOXAMIDE. J Biol Chem. 2015 May 29;290(22):13710-24. doi: 10.1074/jbc.M115.646414. Epub 2015 Apr 8. PMID: 25855790; PMCID: PMC4447950. 10: Siricilla S, Mitachi K, Wan B, Franzblau SG, Kurosu M. Discovery of a capuramycin analog that kills nonreplicating Mycobacterium tuberculosis and its synergistic effects with translocase I inhibitors. J Antibiot (Tokyo). 2015 Apr;68(4):271-8. doi: 10.1038/ja.2014.133. Epub 2014 Oct 1. PMID: 25269459; PMCID: PMC4382465. 11: Wang Y, Siricilla S, Aleiwi BA, Kurosu M. Improved synthesis of capuramycin and its analogues. Chemistry. 2013 Oct 4;19(41):13847-58. doi: 10.1002/chem.201302389. Epub 2013 Sep 6. PMID: 24014478; PMCID: PMC3929971. 12: Wang Y, Kurosu M. A new protecting group and linker for uridine ureido nitrogen. Tetrahedron. 2012 Jun 17;68(24):4797-4804. doi: 10.1016/j.tet.2012.03.121. Epub 2012 Apr 9. PMID: 22711936; PMCID: PMC3375706. 13: Walsh CT, Zhang W. Chemical logic and enzymatic machinery for biological assembly of peptidyl nucleoside antibiotics. ACS Chem Biol. 2011 Oct 21;6(10):1000-7. doi: 10.1021/cb200284p. Epub 2011 Aug 25. PMID: 21851099; PMCID: PMC3199363. 14: Bogatcheva E, Dubuisson T, Protopopova M, Einck L, Nacy CA, Reddy VM. Chemical modification of capuramycins to enhance antibacterial activity. J Antimicrob Chemother. 2011 Mar;66(3):578-87. doi: 10.1093/jac/dkq495. Epub 2010 Dec 23. PMID: 21186194; PMCID: PMC3037154. 15: Dubuisson T, Bogatcheva E, Krishnan MY, Collins MT, Einck L, Nacy CA, Reddy VM. In vitro antimicrobial activities of capuramycin analogues against non- tuberculous mycobacteria. J Antimicrob Chemother. 2010 Dec;65(12):2590-7. doi: 10.1093/jac/dkq372. Epub 2010 Oct 14. PMID: 20952419; PMCID: PMC2976629. 16: Funabashi M, Yang Z, Nonaka K, Hosobuchi M, Fujita Y, Shibata T, Chi X, Van Lanen SG. An ATP-independent strategy for amide bond formation in antibiotic biosynthesis. Nat Chem Biol. 2010 Aug;6(8):581-6. doi: 10.1038/nchembio.393. Epub 2010 Jun 20. PMID: 20562876. 17: Yang Z, Funabashi M, Nonaka K, Hosobuchi M, Shibata T, Pahari P, Van Lanen SG. Functional and kinetic analysis of the phosphotransferase CapP conferring selective self-resistance to capuramycin antibiotics. J Biol Chem. 2010 Apr 23;285(17):12899-905. doi: 10.1074/jbc.M110.104141. Epub 2010 Mar 4. PMID: 20202936; PMCID: PMC2857116. 18: Nikonenko BV, Reddy VM, Protopopova M, Bogatcheva E, Einck L, Nacy CA. Activity of SQ641, a capuramycin analog, in a murine model of tuberculosis. Antimicrob Agents Chemother. 2009 Jul;53(7):3138-9. doi: 10.1128/AAC.00366-09. Epub 2009 May 4. PMID: 19414567; PMCID: PMC2704676. 19: Kurosu M, Li K, Crick DC. Concise synthesis of capuramycin. Org Lett. 2009 Jun 4;11(11):2393-6. doi: 10.1021/ol900458w. PMID: 19405507; PMCID: PMC4784474. 20: Reddy VM, Einck L, Nacy CA. In vitro antimycobacterial activities of capuramycin analogues. Antimicrob Agents Chemother. 2008 Feb;52(2):719-21. doi: 10.1128/AAC.01469-07. Epub 2007 Dec 10. PMID: 18070956; PMCID: PMC2224724.