Ambruticin

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

MedKoo CAT#: 341564

CAS#: 58857-02-6 (freebase)

Description: Ambruticin is a biochemical.

Chemical Structure

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Ambruticin
CAS# 58857-02-6 (freebase)
Instruction

Theoretical Analysis

MedKoo Cat#: 341564
Name: Ambruticin
CAS#: 58857-02-6 (freebase)
Chemical Formula: C28H42O6
Exact Mass: 474.30
Molecular Weight: 474.638
Elemental Analysis: C, 70.86; H, 8.92; O, 20.22

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Related CAS #: 58857-02-6 (freebase)   67999-78-4 (sodium)    

Synonym: Ambruticin; W 7783; W-7783; W7783.

IUPAC/Chemical Name: 5,6-Dihydroxypolyangioic acid

InChi Key: TYIXBSJXUFTELJ-LQJOTGEPSA-N

InChi Code: InChI=1S/C28H42O6/c1-6-24-17(3)8-11-25(34-24)18(4)13-16(2)7-9-21-19(5)22(21)10-12-26-28(32)23(29)14-20(33-26)15-27(30)31/h7-10,12-13,16,19-26,28-29,32H,6,11,14-15H2,1-5H3,(H,30,31)/b9-7+,12-10+,18-13+/t16-,19-,20+,21+,22+,23+,24-,25-,26+,28-/m1/s1

SMILES Code: CC[C@H]1O[C@H](CC=C1C)\C(=C\[C@H](C)\C=C\[C@H]2[C@@H](C)[C@@H]2\C=C\[C@@H]3O[C@H](CC(=O)O)C[C@H](O)[C@H]3O)\C

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 474.64 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Hemmerling F, Lebe KE, Wunderlich J, Hahn F. An Unusual Fatty Acyl:Adenylate Ligase (FAAL)-Acyl Carrier Protein (ACP) Didomain in Ambruticin Biosynthesis. Chembiochem. 2018 Mar 8. doi: 10.1002/cbic.201800084. [Epub ahead of print] PubMed PMID: 29517170.

2: Ma Y, Yun YK, Wondergem Nee Lukesh J, Sar A, Gone JR, Lindeman S, Donaldson WA. Reactivity of (1-methoxycarbonylpentadienyl)iron(1+) cations with hydride, methyl, and nitrogen nucleophiles. Tetrahedron. 2017 Jul 27;73(30):4493-4500. doi: 10.1016/j.tet.2017.06.026. Epub 2017 Jun 15. PubMed PMID: 29200513; PubMed Central PMCID: PMC5703425.

3: Sung KH, Berkhan G, Hollmann T, Wagner L, Blankenfeldt W, Hahn F. Insights into the Dual Activity of a Bifunctional Dehydratase-Cyclase Domain. Angew Chem Int Ed Engl. 2018 Jan 2;57(1):343-347. doi: 10.1002/anie.201707774. Epub 2017 Dec 6. PubMed PMID: 29084363.

4: Berkhan G, Merten C, Holec C, Hahn F. The Interplay between a Multifunctional Dehydratase Domain and a C-Methyltransferase Effects Olefin Shift in Ambruticin Biosynthesis. Angew Chem Int Ed Engl. 2016 Oct 17;55(43):13589-13592. doi: 10.1002/anie.201607827. Epub 2016 Sep 27. PubMed PMID: 27670141.

5: Berkhan G, Hahn F. A dehydratase domain in ambruticin biosynthesis displays additional activity as a pyran-forming cyclase. Angew Chem Int Ed Engl. 2014 Dec 15;53(51):14240-4. doi: 10.1002/anie.201407979. Epub 2014 Oct 19. PubMed PMID: 25327645.

6: Hill P, Piel J, Aris-Brosou S, Krištůfek V, Boddy CN, Dijkhuizen L. Habitat-specific type I polyketide synthases in soils and street sediments. J Ind Microbiol Biotechnol. 2014 Jan;41(1):75-85. doi: 10.1007/s10295-013-1362-7. Epub 2013 Nov 16. PubMed PMID: 24241933.

7: Lee C, An D, Lee H, Cho K. Correlation between Sorangium cellulosum subgroups and their potential for secondary metabolite production. J Microbiol Biotechnol. 2013 Mar;23(3):297-303. PubMed PMID: 23462001.

8: Buschart A, Gremmer K, El-Mowafy M, van den Heuvel J, Mueller PP, Bilitewski U. A novel functional assay for fungal histidine kinases group III reveals the role of HAMP domains for fungicide sensitivity. J Biotechnol. 2012 Jan;157(1):268-77. doi: 10.1016/j.jbiotec.2011.09.017. Epub 2011 Sep 22. PubMed PMID: 21963586.

9: Hanessian S, Focken T, Mi X, Oza R, Chen B, Ritson D, Beaudegnies R. Total synthesis of (+)-ambruticin S: probing the pharmacophoric subunit. J Org Chem. 2010 Aug 20;75(16):5601-18. doi: 10.1021/jo100956v. PubMed PMID: 20704433.

10: Dongo A, Bataillé-Simoneau N, Campion C, Guillemette T, Hamon B, Iacomi-Vasilescu B, Katz L, Simoneau P. The group III two-component histidine kinase of filamentous fungi is involved in the fungicidal activity of the bacterial polyketide ambruticin. Appl Environ Microbiol. 2009 Jan;75(1):127-34. doi: 10.1128/AEM.00993-08. Epub 2008 Nov 14. PubMed PMID: 19011080; PubMed Central PMCID: PMC2612220.

11: Tian ZQ, Wang Z, Xu Y, Tran CQ, Myles DC, Zhong Z, Simmons J, Vetcher L, Katz L, Li Y, Shaw SJ. Investigating amine derivatives of ambruticin VS-5 and VS-4. ChemMedChem. 2008 Jun;3(6):963-9. doi: 10.1002/cmdc.200800008. PubMed PMID: 18307190.

12: Wesolowski J, Hassan RY, Hodde S, Bardroff C, Bilitewski U. Sensing of oxygen in microtiter plates: a novel tool for screening drugs against pathogenic yeasts. Anal Bioanal Chem. 2008 Jul;391(5):1731-7. doi: 10.1007/s00216-008-1947-6. Epub 2008 Feb 24. PubMed PMID: 18297273.

13: Vetcher L, Menzella HG, Kudo T, Motoyama T, Katz L. The antifungal polyketide ambruticin targets the HOG pathway. Antimicrob Agents Chemother. 2007 Oct;51(10):3734-6. Epub 2007 Aug 13. PubMed PMID: 17698623; PubMed Central PMCID: PMC2043265.

14: Julien B, Tian ZQ, Reid R, Reeves CD. Analysis of the ambruticin and jerangolid gene clusters of Sorangium cellulosum reveals unusual mechanisms of polyketide biosynthesis. Chem Biol. 2006 Dec;13(12):1277-86. PubMed PMID: 17185223.

15: Shubitz LF, Galgiani JN, Tian ZQ, Zhong Z, Timmermans P, Katz L. Efficacy of ambruticin analogs in a murine model of coccidioidomycosis. Antimicrob Agents Chemother. 2006 Oct;50(10):3467-9. PubMed PMID: 17005834; PubMed Central PMCID: PMC1610061.

16: Chiang LY, Ejzykowicz DE, Tian ZQ, Katz L, Filler SG. Efficacy of ambruticin analogs in a murine model of invasive pulmonary aspergillosis. Antimicrob Agents Chemother. 2006 Oct;50(10):3464-6. PubMed PMID: 17005833; PubMed Central PMCID: PMC1610070.

17: Xu Y, Wang Z, Tian ZQ, Li Y, Shaw SJ. Investigating carboxylic acid analogues of ambruticin through semi-synthesis. ChemMedChem. 2006 Oct;1(10):1063-5. PubMed PMID: 16929556.

18: Pospísil J, Kumamoto T, Markó IE. Highly diastereoselective silyl-modified sakurai multicomponent reaction. Angew Chem Int Ed Engl. 2006 May 12;45(20):3357-60. PubMed PMID: 16604570.

19: Lukesh JM, Donaldson WA. Synthesis of cyclopropanes via organoiron methodology: preparation of the C9-C16 alkenylcyclopropane segment of ambruticin. Chem Commun (Camb). 2005 Jan 7;(1):110-2. Epub 2004 Nov 23. PubMed PMID: 15614389.

20: Taylor MS, Jacobsen EN. Asymmetric catalysis in complex target synthesis. Proc Natl Acad Sci U S A. 2004 Apr 13;101(15):5368-73. Epub 2004 Mar 12. Review. PubMed PMID: 15020767; PubMed Central PMCID: PMC397387.