MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 525277 | Name: Showdomycin

Description:

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

Showdomycin is an antineoplastic antibiotic.

Chemical Structure

Showdomycin
Showdomycin
CAS#16755-07-0

Theoretical Analysis

MedKoo Cat#: 525277

Name: Showdomycin

CAS#: 16755-07-0

Chemical Formula: C9H11NO6

Exact Mass: 229.0586

Molecular Weight: 229.19

Elemental Analysis: C, 47.17; H, 4.84; N, 6.11; O, 41.88

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
Showdomycin
IUPAC/Chemical Name
2-beta-D-Ribofuranosylmaleimide; 3-[(2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrole-2,5-dione
InChi Key
FFLUMYXAPXARJP-JBBNEOJLSA-N
InChi Code
InChI=1S/C9H11NO6/c11-2-4-6(13)7(14)8(16-4)3-1-5(12)10-9(3)15/h1,4,6-8,11,13-14H,2H2,(H,10,12,15)/t4-,6-,7-,8+/m1/s1
SMILES Code
O=C(NC1=O)C=C1[C@H]2[C@H](O)[C@H](O)[C@@H](CO)O2
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
>2 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 229.19 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: Palmu K, Rosenqvist P, Thapa K, Ilina Y, Siitonen V, Baral B, Mäkinen J, Belogurov G, Virta P, Niemi J, Metsä-Ketelä M. Discovery of the Showdomycin Gene Cluster from Streptomyces showdoensis ATCC 15227 Yields Insight into the Biosynthetic Logic of C-Nucleoside Antibiotics. ACS Chem Biol. 2017 Apr 27. doi: 10.1021/acschembio.7b00078. [Epub ahead of print] PubMed PMID: 28418235. 2: De Clercq E. C-Nucleosides To Be Revisited. J Med Chem. 2016 Mar 24;59(6):2301-11. doi: 10.1021/acs.jmedchem.5b01157. Epub 2015 Oct 29. Review. PubMed PMID: 26513594. 3: Rudolf GC, Koch MF, Mandl FA, Sieber SA. Subclass-specific labeling of protein-reactive natural products with customized nucleophilic probes. Chemistry. 2015 Feb 23;21(9):3701-7. doi: 10.1002/chem.201405009. Epub 2015 Jan 21. PubMed PMID: 25605563. 4: Böttcher T, Sieber SA. Showdomycin as a versatile chemical tool for the detection of pathogenesis-associated enzymes in bacteria. J Am Chem Soc. 2010 May 26;132(20):6964-72. doi: 10.1021/ja909150y. PubMed PMID: 20433172. 5: Naz A, Bano K, Bano F, Ghafoor NA, Akhtar N. Conformational analysis (geometry optimization) of nucleosidic antitumor antibiotic showdomycin by Arguslab 4 software. Pak J Pharm Sci. 2009 Jan;22(1):78-82. PubMed PMID: 19168426. 6: Trost BM, Kallander LS. A Versatile Enantioselective Strategy Toward L-C-Nucleosides: A Total Synthesis of L-Showdomycin. J Org Chem. 1999 Jul 23;64(15):5427-5435. PubMed PMID: 11674603. 7: Kean EL, Wei Z, Anderson VE, Zhang N, Sayre LM. Regulation of the biosynthesis of N-acetylglucosaminylpyrophosphoryldolichol, feedback and product inhibition. J Biol Chem. 1999 Nov 26;274(48):34072-82. PubMed PMID: 10567375. 8: Kitani S, Kinoshita H, Nihira T, Yamada Y. In vitro analysis of the butyrolactone autoregulator receptor protein (FarA) of Streptomyces lavendulae FRI-5 reveals that FarA acts as a DNA-binding transcriptional regulator that controls its own synthesis. J Bacteriol. 1999 Aug;181(16):5081-4. PubMed PMID: 10438782; PubMed Central PMCID: PMC93999. 9: Kean EL, Wei Z. Stimulation as well as inhibition by antibiotics of the formation of GlcNAc-lipids of the dolichol pathway. Glycoconj J. 1998 Apr;15(4):405-14. PubMed PMID: 9613828. 10: Ruengjitchatchawalya M, Nihira T, Yamada Y. Purification and characterization of the IM-2-binding protein from Streptomyces sp. strain FRI-5. J Bacteriol. 1995 Feb;177(3):551-7. PubMed PMID: 7836286; PubMed Central PMCID: PMC176627. 11: Mumper MW, Aurenge C, Hosmane RS. "Slim" nucleosides and nucleotides. I. Synthetic, structural and biophysical investigations of showdomycins. J Biomol Struct Dyn. 1994 Apr;11(5):1107-31. PubMed PMID: 7524539. 12: Dagnino L, Bennett LL Jr, Paterson AR. Substrate specificity, kinetics, and stoichiometry of sodium-dependent adenosine transport in L1210/AM mouse leukemia cells. J Biol Chem. 1991 Apr 5;266(10):6312-7. PubMed PMID: 1848853. 13: Takahashi T, Kotsubo H, Koizumi T. Enantioselective synthesis of a novel carbocyclic C-nucleoside via asymmetric Diels-Alder reaction of (S)s-3-(2-pyridylsulfinyl)-acrylate. Nucleic Acids Symp Ser. 1991;(25):187-8. PubMed PMID: 1669484. 14: Rauter AP, Figueiredo JA, Ismael IM. Synthesis of pseudo-C-nucleosides. Carbohydr Res. 1989 Jun 1;188:19-24. PubMed PMID: 2776128. 15: Yamashita T, Saito K. No direct involvement of plasma membrane divalent cation-activated adenosine triphosphatase in histamine release from rat mast cells. Biochem Biophys Res Commun. 1987 Apr 29;144(2):951-6. PubMed PMID: 2437921. 16: Kaushal GP, Elbein AD. Properties of Solubilized UDP-GlcNAc: Dolichyl Phosphate-GlcNAc-1-P-Transferase from Soybean Cultured Cells. Plant Physiol. 1986 Nov;82(3):748-52. PubMed PMID: 16665105; PubMed Central PMCID: PMC1056202. 17: Takatsuki A, Tamura G. [Inhibitors affecting synthesis and intracellular translocation of glycoproteins as probes]. Tanpakushitsu Kakusan Koso. 1985 Jun;30(6):417-40. Review. Japanese. PubMed PMID: 2930868. 18: Hacksell U, Daves GD Jr. The chemistry and biochemistry of C-nucleosides and C-arylglycosides. Prog Med Chem. 1985;22:1-65. Review. PubMed PMID: 3915364. 19: Ohno M. Creation of novel chiral synthons with enzymes: application to enantioselective synthesis of antibiotics. Ciba Found Symp. 1985;111:171-87. PubMed PMID: 3874758. 20: Yamashita T, Someya A, Tsuzawa-Kido Y. Effect of maleimide derivatives on superoxide-generating system of guinea-pig neutrophils stimulated by different soluble stimuli. Eur J Biochem. 1984 Nov 15;145(1):71-6. PubMed PMID: 6092085.