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MedKoo Cat#: 596501 | Name: Amiclenomycin

Description:

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

Amiclenomycin is an antibiotic isolated from Streptomyces lavendulae subsp. amiclenomycini Okami; active against mycobacterium; activity reversed by biotin & desthiobiotin.

Chemical Structure

Amiclenomycin
Amiclenomycin
CAS#53696-70-1

Theoretical Analysis

MedKoo Cat#: 596501

Name: Amiclenomycin

CAS#: 53696-70-1

Chemical Formula: C10H16N2O2

Exact Mass: 196.1212

Molecular Weight: 196.25

Elemental Analysis: C, 61.20; H, 8.22; N, 14.27; O, 16.30

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
Amiclenomycin; BRN 5525177; BRN-5525177; BRN5525177; NSC 246130; NSC-246130; NSC246130;
IUPAC/Chemical Name
(S)-2-amino-4-((1s,4R)-4-aminocyclohexa-2,5-dien-1-yl)butanoic acid
InChi Key
LAJWZJCOWPUSOA-YIZRAAEISA-N
InChi Code
InChI=1S/C10H16N2O2/c11-8-4-1-7(2-5-8)3-6-9(12)10(13)14/h1-2,4-5,7-9H,3,6,11-12H2,(H,13,14)/t7-,8+,9-/m0/s1
SMILES Code
O=C(O)C(N)CCC1C=CC(N)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
>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 196.25 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: Gehrke SS, Kumar G, Yokubynas NA, Côté JP, Wang W, French S, MacNair CR, Wright GD, Brown ED. Exploiting the Sensitivity of Nutrient Transporter Deletion Strains in Discovery of Natural Product Antimetabolites. ACS Infect Dis. 2017 Dec 8;3(12):955-965. doi: 10.1021/acsinfecdis.7b00149. Epub 2017 Nov 7. PubMed PMID: 29069544. 2: Eiden CG, Aldrich CC. Synthesis of a 3-Amino-2,3-dihydropyrid-4-one and Related Heterocyclic Analogues as Mechanism-Based Inhibitors of BioA, a Pyridoxal Phosphate-Dependent Enzyme. J Org Chem. 2017 Aug 4;82(15):7806-7819. doi: 10.1021/acs.joc.7b00847. Epub 2017 Jul 26. PubMed PMID: 28682613; PubMed Central PMCID: PMC5590672. 3: Shi C, Aldrich CC. Design and synthesis of potential mechanism-based inhibitors of the aminotransferase BioA involved in biotin biosynthesis. J Org Chem. 2012 Jul 20;77(14):6051-8. doi: 10.1021/jo3008435. Epub 2012 Jul 3. PubMed PMID: 22724679; PubMed Central PMCID: PMC3448953. 4: Mann S, Ploux O. Pyridoxal-5'-phosphate-dependent enzymes involved in biotin biosynthesis: structure, reaction mechanism and inhibition. Biochim Biophys Acta. 2011 Nov;1814(11):1459-66. doi: 10.1016/j.bbapap.2010.12.004. Epub 2010 Dec 21. Review. PubMed PMID: 21182990. 5: Prathipati P, Ma NL, Manjunatha UH, Bender A. Fishing the target of antitubercular compounds: in silico target deconvolution model development and validation. J Proteome Res. 2009 Jun;8(6):2788-98. doi: 10.1021/pr8010843. PubMed PMID: 19301903. 6: Mann S, Ploux O. 7,8-Diaminoperlargonic acid aminotransferase from Mycobacterium tuberculosis, a potential therapeutic target. Characterization and inhibition studies. FEBS J. 2006 Oct;273(20):4778-89. Epub 2006 Sep 19. PubMed PMID: 16984394. 7: Mann S, Marquet A, Ploux O. Inhibition of 7,8-diaminopelargonic acid aminotransferase by amiclenomycin and analogues. Biochem Soc Trans. 2005 Aug;33(Pt 4):802-5. Review. PubMed PMID: 16042602. 8: Sandmark J, Mann S, Marquet A, Schneider G. Structural basis for the inhibition of the biosynthesis of biotin by the antibiotic amiclenomycin. J Biol Chem. 2002 Nov 8;277(45):43352-8. Epub 2002 Sep 5. PubMed PMID: 12218056. 9: Mann S, Carillon S, Breyne O, Marquet A. Total synthesis of amiclenomycin, an inhibitor of biotin biosynthesis. Chemistry. 2002 Jan 18;8(2):439-50. PubMed PMID: 11843156. 10: Yamada T, Osawa T, Kawakishi S, Udaka S, Ohta T. Antimutagenic effects of N-methyl-valyl-amiclenomycin (BA-2) isolated from the metabolites of Streptomyces sp. Mutat Res. 1993 Apr;286(2):293-7. PubMed PMID: 7681541. 11: Poetsch M, Zähner H, Werner RG, Kern A, Jung G. Metabolic products from microorganisms. 230. Amiclenomycin-peptides, new antimetabolites of biotin. Taxonomy, fermentation and biological properties. J Antibiot (Tokyo). 1985 Mar;38(3):312-20. PubMed PMID: 3891702. 12: Hotta K, Kitahara T, Okami Y. Studies of the mode of action of amiclenomycin. J Antibiot (Tokyo). 1975 Mar;28(3):222-8. PubMed PMID: 805119. 13: Kitahara T, Hotta K, Yoshida M, Okami Y. Biological studies of amiclenomycin. J Antibiot (Tokyo). 1975 Mar;28(3):215-21. PubMed PMID: 805118. 14: Okami Y, Kitahara T, Hamada M, Naganawa H, Kondo S. Studies on a new amino acid antibiotic, amiclenomycin. J Antibiot (Tokyo). 1974 Sep;27(9):656-64. PubMed PMID: 4436150.