Aklavinone

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

MedKoo CAT#: 592375

CAS#: 16234-96-1

Description: Aklavinone is a biochemical.

Chemical Structure

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Aklavinone
CAS# 16234-96-1
Instruction

Theoretical Analysis

MedKoo Cat#: 592375
Name: Aklavinone
CAS#: 16234-96-1
Chemical Formula: C22H20O8
Exact Mass: 412.12
Molecular Weight: 412.390
Elemental Analysis: C, 64.08; H, 4.89; O, 31.04

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

Synonym: Aklavinone; NSC 114780; NSC-114780; NSC114780

IUPAC/Chemical Name: 1-Naphthacenecarboxylic acid, 2-ethyl-1,2,3,4,6,11-hexahydro-2,4,5,7-tetrahydroxy-6,11-dioxo-, methyl ester, (1R,2R,4S)- (8CI)

InChi Key: RACGRCLGVYXIAO-YOKWENHESA-N

InChi Code: InChI=1S/C22H20O8/c1-3-22(29)8-13(24)15-10(17(22)21(28)30-2)7-11-16(20(15)27)19(26)14-9(18(11)25)5-4-6-12(14)23/h4-7,13,17,23-24,27,29H,3,8H2,1-2H3/t13-,17-,22+/m0/s1

SMILES Code: O=C([C@H]1[C@@](O)(CC)C[C@H](O)C(C(O)=C2C(C3=C4C=CC=C3O)=O)=C1C=C2C4=O)OC

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 412.39 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: Kim E, Song MC, Kim MS, Beom JY, Jung JA, Cho HS, Yoon YJ. One-Pot Combinatorial Biosynthesis of Glycosylated Anthracyclines by Cocultivation of Streptomyces Strains Producing Aglycones and Nucleotide Deoxysugars. ACS Comb Sci. 2017 Apr 10;19(4):262-270. doi: 10.1021/acscombsci.6b00194. Epub 2017 Feb 22. PubMed PMID: 28191923.

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3: Türker L. Tautomerism in 11-hydroxyaklavinone: a DFT study. ScientificWorldJournal. 2012;2012:526289. doi: 10.1100/2012/526289. Epub 2012 May 1. PubMed PMID: 22623911; PubMed Central PMCID: PMC3353482.

4: Lindqvist Y, Koskiniemi H, Jansson A, Sandalova T, Schnell R, Liu Z, Mäntsälä P, Niemi J, Schneider G. Structural basis for substrate recognition and specificity in aklavinone-11-hydroxylase from rhodomycin biosynthesis. J Mol Biol. 2009 Nov 6;393(4):966-77. doi: 10.1016/j.jmb.2009.09.003. Epub 2009 Sep 8. PubMed PMID: 19744497.

5: Lu W, Leimkuhler C, Gatto GJ Jr, Kruger RG, Oberthür M, Kahne D, Walsh CT. AknT is an activating protein for the glycosyltransferase AknS in L-aminodeoxysugar transfer to the aglycone of aclacinomycin A. Chem Biol. 2005 May;12(5):527-34. PubMed PMID: 15911373.

6: Clark B, Capon RJ, Stewart M, Lacey E, Tennant S, Gill JH. Blanchaquinone: a new anthraquinone from an Australian Streptomyces sp. J Nat Prod. 2004 Oct;67(10):1729-31. PubMed PMID: 15497950.

7: Lu W, Leimkuhler C, Oberthür M, Kahne D, Walsh CT. AknK is an L-2-deoxyfucosyltransferase in the biosynthesis of the anthracycline aclacinomycin A. Biochemistry. 2004 Apr 20;43(15):4548-58. PubMed PMID: 15078101.

8: Jansson A, Niemi J, Mäntsälä P, Schneider G. Crystal structure of aclacinomycin methylesterase with bound product analogues: implications for anthracycline recognition and mechanism. J Biol Chem. 2003 Oct 3;278(40):39006-13. Epub 2003 Jul 23. PubMed PMID: 12878604.

9: Räty K, Hautala A, Torkkell S, Kantola J, Mäntsälä P, Hakala J, Ylihonko K. Characterization of mutations in aclacinomycin A-non-producing Streptomyces galilaeus strains with altered glycosylation patterns. Microbiology. 2002 Nov;148(Pt 11):3375-84. PubMed PMID: 12427929.

10: Chung JY, Fujii I, Harada S, Sankawa U, Ebizuka Y. Expression, purification, and characterization of AknX anthrone oxygenase, which is involved in aklavinone biosynthesis in Streptomyces galilaeus. J Bacteriol. 2002 Nov;184(22):6115-22. PubMed PMID: 12399480; PubMed Central PMCID: PMC151955.

11: Räty K, Kantola J, Hautala A, Hakala J, Ylihonko K, Mäntsälä P. Cloning and characterization of Streptomyces galilaeus aclacinomycins polyketide synthase (PKS) cluster. Gene. 2002 Jun 26;293(1-2):115-22. PubMed PMID: 12137949.

12: Wang Y, Niemi J, Mäntsälä P. Modification of aklavinone and aclacinomycins in vitro and in vivo by rhodomycin biosynthesis gene products. FEMS Microbiol Lett. 2002 Feb 19;208(1):117-22. PubMed PMID: 11934504.

13: Räty K, Kunnari T, Hakala J, Mäntsälä P, Ylihonko K. A gene cluster from Streptomyces galilaeus involved in glycosylation of aclarubicin. Mol Gen Genet. 2000 Sep;264(1-2):164-72. PubMed PMID: 11016846.

14: Niemi J, Wang Y, Airas K, Ylihonko K, Hakala J, Mäntsälä P. Characterization of aklavinone-11-hydroxylase from Streptomyces purpurascens. Biochim Biophys Acta. 1999 Feb 10;1430(1):57-64. PubMed PMID: 10082933.

15: Katayama J, Noguchi N. Nucleotide sequence of the gene cluster containing the mphB gene for macrolide 2'-phosphotransferase II. Biol Pharm Bull. 1999 Feb;22(2):227-8. PubMed PMID: 10077450.

16: Kantola J, Blanco G, Hautala A, Kunnari T, Hakala J, Mendez C, Ylihonko K, Mäntsälä P, Salas J. Folding of the polyketide chain is not dictated by minimal polyketide synthase in the biosynthesis of mithramycin and anthracycline. Chem Biol. 1997 Oct;4(10):751-5. PubMed PMID: 9375253.

17: Johdo O, Yoshioka T, Naganawa H, Takeuchi T, Yoshimoto A. New betaclamycin and aclarubicin analogs obtained by prolonged microbial conversion with an aclarubicin-negative mutant. J Antibiot (Tokyo). 1996 Jul;49(7):669-75. PubMed PMID: 8784429.

18: Dickens ML, Ye J, Strohl WR. Cloning, sequencing, and analysis of aklaviketone reductase from Streptomyces sp. strain C5. J Bacteriol. 1996 Jun;178(11):3384-8. PubMed PMID: 8655529; PubMed Central PMCID: PMC178101.

19: Kim HS, Kim YH, Yoo OJ, Lee JJ. Aclacinomycin X, a novel anthracycline antibiotic produced by Streptomyces galilaeus ATCC 31133. Biosci Biotechnol Biochem. 1996 May;60(5):906-8. PubMed PMID: 8704322.

20: Kim HS, Hong YS, Kim YH, Yoo OJ, Lee JJ. New anthracycline metabolites produced by the aklavinone 11-hydroxylase gene in Streptomyces galilaeus ATCC 31133. J Antibiot (Tokyo). 1996 Apr;49(4):355-60. PubMed PMID: 8641998.