MedKoo Cat#: 598149 | Name: Furanomycin

Description:

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

Furanomycin is an isoleucine—tRNA ligase inhibitor. Furanomycin is a Streptomyces metabolite that substitutes for isoleucine in protein translation. Furanomycin is a secondary metabolite of SBW25. This compound was also known as a natural product produced by a strain of Streptomyces.

Chemical Structure

Furanomycin
Furanomycin
CAS#18455-25-9

Theoretical Analysis

MedKoo Cat#: 598149

Name: Furanomycin

CAS#: 18455-25-9

Chemical Formula: C7H11NO3

Exact Mass: 157.0739

Molecular Weight: 157.16

Elemental Analysis: C, 53.49; H, 7.05; N, 8.91; O, 30.54

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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Related CAS #
No Data
Synonym
Furanomycin; NSC 116328; NSC-116328; NSC116328;
IUPAC/Chemical Name
(S)-2-amino-2-((2R,5S)-5-methyl-2,5-dihydrofuran-2-yl)acetic acid
InChi Key
PNOKUGWGMLEAPE-JKUQZMGJSA-N
InChi Code
InChI=1S/C7H11NO3/c1-4-2-3-5(11-4)6(8)7(9)10/h2-6H,8H2,1H3,(H,9,10)/t4-,5+,6-/m0/s1
SMILES Code
O=C(O)[C@@H](N)[C@@H]1O[C@@H](C)C=C1
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 157.16 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: Jung JH, Yoon DH, Lee K, Shin H, Lee WK, Yook CM, Ha HJ. Stereoselective Pd-catalyzed etherification and asymmetric synthesis of furanomycin and its analogues from a chiral aziridine. Org Biomol Chem. 2015 Aug 14;13(30):8187-95. doi: 10.1039/c5ob00375j. PubMed PMID: 26054629. 2: Trippe K, McPhail K, Armstrong D, Azevedo M, Banowetz G. Pseudomonas fluorescens SBW25 produces furanomycin, a non-proteinogenic amino acid with selective antimicrobial properties. BMC Microbiol. 2013 May 20;13:111. doi: 10.1186/1471-2180-13-111. Erratum in: BMC Microbiol. 2013;13:263. PubMed PMID: 23688329; PubMed Central PMCID: PMC3662646. 3: Kohno T, Kohda D, Haruki M, Yokoyama S, Miyazawa T. Nonprotein amino acid furanomycin, unlike isoleucine in chemical structure, is charged to isoleucine tRNA by isoleucyl-tRNA synthetase and incorporated into protein. J Biol Chem. 1990 Apr 25;265(12):6931-5. PubMed PMID: 2182633. 4: VanBrunt MP, Standaert RF. A short total synthesis of (+)-furanomycin. Org Lett. 2000 Mar 9;2(5):705-8. PubMed PMID: 10814415. 5: Parry RJ, Yang N. Isolation and characterization of furanomycin nonproducing Streptomyces threomyceticus mutants. J Antibiot (Tokyo). 1992 Jul;45(7):1161-6. PubMed PMID: 1517161. 6: Kazmaier U, Pähler S, Endermann R, Häbich D, Kroll HP, Riedl B. Straightforward syntheses of furanomycin derivatives and their biological evaluation. Bioorg Med Chem. 2002 Dec;10(12):3905-13. PubMed PMID: 12413842. 7: Lee JY, Schiffer G, Jäger V. Synthesis of L-carbafuranomycin, an unnatural analogue of the antibiotic amino acid furanomycin. Org Lett. 2005 Jun 9;7(12):2317-20. PubMed PMID: 15932187. 8: Avenoza A, Busto JH, Canal N, Corzana F, Peregrina JM, Pérez-Fernández M, Rodríguez F. Cyclobutane amino acid analogues of furanomycin obtained by a formal [2 + 2] cycloaddition strategy promoted by methylaluminoxane. J Org Chem. 2010 Feb 5;75(3):545-52. doi: 10.1021/jo9025258. PubMed PMID: 20038109. 9: Katagiri K, Tori K, Kimura Y, Yoshida T, Nagasaki T, Minato H. A new antibiotic. Furanomycin, an isoleucine antagonist. J Med Chem. 1967 Nov;10(6):1149-54. PubMed PMID: 4861779. 10: Tanaka K, Tamaki M, Watanabe S. Effect of furanomycin on the synthesis of isoleucyl-tRNA. Biochim Biophys Acta. 1969 Nov 19;195(1):244-5. PubMed PMID: 4982424. 11: Zhang J, Clive DL. Synthesis of (+)-Furanomycin: Use of Radical Cyclization. J Org Chem. 1999 Mar 5;64(5):1754-1757. PubMed PMID: 11674252. 12: Zimmermann PJ, Blanarikova I I, Jäger V V. A General Approach to L-(+)-Furanomycin and Some Stereoisomers and Analogues Using Furoisoxazoline Intermediates Syntheses via Isoxazolines, Part 24. Part of the planned dissertation of P. J. Zimmermann. We thank the Volkswagen-Stiftung, Hannover, the Fonds der Chemischen Industrie, the Landesgraduiertenförderung Baden-Württemberg (doctoral fellowship to P.J.Z.), and Bayer AG, Wuppertal, for financial support of this work. I.B. gratefully acknowledges a grant from the Volkswagen-Stiftung for a research stay at Stuttgart. We thank Dr. W. Frey for the X-ray crystal structure determinations. This work was presented at the 17th ICHC, Vienna, in August 1999, Book of Abstracts OP-61. Part 23: ref. 1. Angew Chem Int Ed Engl. 2000 Mar;39(5):910-912. PubMed PMID: 10760890. 13: Nelson JM, Vedejs E. Metalated aziridines for cross-coupling with aryl and alkenyl halides via palladium catalysis. Org Lett. 2010 Nov 19;12(22):5085-7. doi: 10.1021/ol101904a. Epub 2010 Oct 14. PubMed PMID: 20945857; PubMed Central PMCID: PMC2996137. 14: Erdsack J, Krause N. An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine. Beilstein J Org Chem. 2013 Sep 25;9:1936-42. doi: 10.3762/bjoc.9.229. eCollection 2013. PubMed PMID: 24204404; PubMed Central PMCID: PMC3817573. 15: Erdsack J, Schürmann M, Preut H, Krause N. (1R,4'S)-4-(tert-Butyl-dimethyl-silan-oxy)-1-[2,2-dimethyl-3-(p-tolyl-sulfon-yl)- 1,3-oxazolidin-4-yl]but-2-yn-1-ol. Acta Crystallogr Sect E Struct Rep Online. 2008 May 30;64(Pt 6):o1171. doi: 10.1107/S1600536808014906. PubMed PMID: 21202678; PubMed Central PMCID: PMC2961448. 16: Hughes J, Mellows G. Inhibition of isoleucyl-transfer ribonucleic acid synthetase in Escherichia coli by pseudomonic acid. Biochem J. 1978 Oct 15;176(1):305-18. PubMed PMID: 365175; PubMed Central PMCID: PMC1186229.