MedKoo Cat#: 146195 | Name: Sarkomycin

Description:

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

Sarkomycin is a natural antibiotic compound derived from Streptomyces species, known for its potent antitumor and antimicrobial activities. It works by inhibiting DNA synthesis and inducing cell cycle arrest, which ultimately leads to the apoptosis of cancer cells. Sarkomycin's mechanism involves the disruption of DNA replication by interfering with enzymes such as topoisomerases, which are crucial for maintaining DNA structure during cell division. Due to these properties, it is being studied for potential use in cancer therapy and as an antimicrobial agent.

Chemical Structure

Sarkomycin
Sarkomycin
CAS#489-21-4

Theoretical Analysis

MedKoo Cat#: 146195

Name: Sarkomycin

CAS#: 489-21-4

Chemical Formula: C7H15NO

Exact Mass: 129.1154

Molecular Weight: 129.20

Elemental Analysis: C, 65.07; H, 11.70; N, 10.84; O, 12.38

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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Synonym
Sarkomycin;
IUPAC/Chemical Name
(S)-2-methylene-3-oxocyclopentane-1-carboxylic acid
InChi Key
ILFPCMXTASDZKM-YFKPBYRVSA-N
InChi Code
1S/C7H8O3/c1-4-5(7(9)10)2-3-6(4)8/h5H,1-3H2,(H,9,10)/t5-/m0/s1
SMILES Code
OC(=O)[C@H]1CCC(=O)C1=C
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 129.20 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: KONDO S. [SARKOMYCIN AS OF DECEMBER 1961]. J Antibiot B. 1963 Jun;16:210-9. Japanese. PMID: 14043983. 2: ISHIYAMA S. [Sarkomycin]. Gan. 1956 Dec;47(3-4):444-5. Japanese. PMID: 13415076. 3: UMEZAWA H, YAMAMOTO T, TAKEUCHI T, OSATO T, OKAMI Y, YAMAOKA S, OKUDA T, NITTA K, YAGISHITA K, UTAHARA R, UMEZAWA S. Sarkomycin, and anti-cancer substance produced by Stroptomyces. Antibiot Chemother (Northfield). 1954 May;4(5):514-20. PMID: 24543024. 4: Hill RK, Foley PJ Jr, Gardella LA. The absolute configuration of sarkomycin. J Org Chem. 1967 Jul;32(7):2330-5. doi: 10.1021/jo01282a052. PMID: 6046180. 5: TOKI K, WADA H, SUZUKI Y, SAITO C. Synthesis of sarkomycin. J Antibiot (Tokyo). 1957 Jan;10(1):35. PMID: 13449006. 6: Liu LF, Qi H, Zhang H, Wang JD, Yu NF. A new sarkomycin analog from Streptomyces sp. HS-HY-144. J Antibiot (Tokyo). 2015 Dec;68(12):760-2. doi: 10.1038/ja.2015.66. Epub 2015 Jun 10. PMID: 26058568. 7: KEIR HM, SHEPHERD JB. THIOL GROUPS IN DEOXYRIBONUCLEIC ACID NUCLEOTIDYLTRANSFERASE. Biochem J. 1965 May;95(2):483-9. doi: 10.1042/bj0950483. PMID: 14340098; PMCID: PMC1214347. 8: HOOPER IR, CHENEY LC, CRON MJ, FARDIG OB, JOHNSON DA, JOHNSON DL, PALERMITI FM, SCHMITZ H, WHEATLE WB. Studies on sarkomycin. Antibiot Chemother (Northfield). 1955 Oct;5(10):585-95. PMID: 24543775. 9: Westmeier J, Kress S, Pfaff C, von Zezschwitz P. Total synthesis of (R)-sarkomycin via asymmetric rhodium-catalyzed conjugate addition. J Org Chem. 2013 Nov 1;78(21):10718-23. doi: 10.1021/jo4016979. Epub 2013 Oct 14. PMID: 24079484. 10: Cabré A, Khaizourane H, Garçon M, Verdaguer X, Riera A. Total Synthesis of ( R)-Sarkomycin Methyl Ester via Regioselective Intermolecular Pauson-Khand Reaction and Iridium-Catalyzed Asymmetric Isomerization. Org Lett. 2018 Jul 6;20(13):3953-3957. doi: 10.1021/acs.orglett.8b01525. Epub 2018 Jun 15. PMID: 29905075. 11: AKITA E, HARA T, YAMADA Y. Studies on sarkomycin. VII. Effects of sarkomycin and related compounds on the anaerobic fermentation of Ehrlich ascites carcinoma cells of mice. J Antibiot (Tokyo). 1956 Sep;9(5):191-2. PMID: 13385197. 12: ISHIYAMA S, ISHIYAMA I, SAKURAI H, FUJII R, SHIRASUGA Y. Concentration of sarkomycin in the body fluid and its urinary excretion, preliminary report. J Antibiot (Tokyo). 1955 Jan;8(1):22-5. PMID: 14367229. 13: TANAKADATE Y, HASEGAWA S, OHASHI I, SAKAI F, NAKASEKO H. [Cytostatic effect of antibiotics (actinomycin J, sarkomycin and pluramycin) on Yoshida ascites sarcoma cells]. Gan. 1956 Dec;47(3-4):357-8. Japanese. PMID: 13415038. 14: Hatano M, Sakamoto T, Mizuno T, Goto Y, Ishihara K. Chiral Supramolecular U-Shaped Catalysts Induce the Multiselective Diels-Alder Reaction of Propargyl Aldehyde. J Am Chem Soc. 2018 Nov 28;140(47):16253-16263. doi: 10.1021/jacs.8b09974. Epub 2018 Nov 15. PMID: 30404439. 15: UMEZAWA H, TAKEUCHI T, NITTA K, YAMAMOTO T, YAMAOKA S. Sarkomycin, an anti- tumor substance produced by streptomyces. J Antibiot (Tokyo). 1953 Apr;6(2):101. PMID: 13084510. 16: Rebroš M, Lipták L, Rosenberg M, Bučko M, Gemeiner P. Biocatalysis with Escherichia coli-overexpressing cyclopentanone monooxygenase immobilized in polyvinyl alcohol gel. Lett Appl Microbiol. 2014 Jun;58(6):556-63. doi: 10.1111/lam.12227. Epub 2014 Feb 24. PMID: 24494800. 17: Kondo S, Nakamura H, Ikeda Y, Naganawa H, Maeda K, Takeuchi T. Structures of two remarkable dimerization products of sarkomycin. J Antibiot (Tokyo). 1997 Apr;50(4):363-5. doi: 10.7164/antibiotics.50.363. PMID: 9186566. 18: Königsberger K, Griengl H. Microbial Baeyer-Villiger reaction of bicyclo[3.2.0]heptan-6-ones--a novel approach to sarkomycin A. Bioorg Med Chem. 1994 Jul;2(7):595-604. doi: 10.1016/0968-0896(94)85006-2. PMID: 7858964. 19: TAKEUCHI T, HIKIJI T, NITTA K, MORIKUBO Y, UMEZAWA H. On antitumor effect of sarkomycin-INH. J Antibiot (Tokyo). 1958 Sep;11(9):212-6. PMID: 13610779. 20: Koenuma M, Kinashi H, Otake N. An improved screening method for antiphage antibiotics and isolation of sarkomycin and its relatives. J Antibiot (Tokyo). 1974 Oct;27(10):801-4. doi: 10.7164/antibiotics.27.801. PMID: 4457528.