Aklanonic acid

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

MedKoo CAT#: 592378

CAS#: 91432-47-2

Description: Aklanonic acid comes from Streptomyces sp. ZIMET 43717; intermediate in biosynthesis of anthracycline antibiotics.


Chemical Structure

img
Aklanonic acid
CAS# 91432-47-2

Theoretical Analysis

MedKoo Cat#: 592378
Name: Aklanonic acid
CAS#: 91432-47-2
Chemical Formula: C21H16O8
Exact Mass: 396.08
Molecular Weight: 396.350
Elemental Analysis: C, 63.64; H, 4.07; O, 32.29

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: Aklanonic acid

IUPAC/Chemical Name: Systematic Name 2-Anthraceneacetic acid, 9,10-dihydro-4,5-dihydroxy-3-(1-hydroxy-3-oxo-1-pentenyl)-9,10-dioxo

InChi Key: WTCFRKORYWVLAQ-ZSOIEALJSA-N

InChi Code: InChI=1S/C21H16O8/c1-2-10(22)8-14(24)16-9(7-15(25)26)6-12-18(20(16)28)21(29)17-11(19(12)27)4-3-5-13(17)23/h3-6,8,23-24,28H,2,7H2,1H3,(H,25,26)/b14-8-

SMILES Code: O=C(O)CC(C=C1C2=O)=C(/C(O)=C/C(CC)=O)C(O)=C1C(C3=C2C=CC=C3O)=O

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 396.35 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:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Castaldo G, Zucko J, Heidelberger S, Vujaklija D, Hranueli D, Cullum J, Wattana-Amorn P, Crump MP, Crosby J, Long PF. Proposed arrangement of proteins forming a bacterial type II polyketide synthase. Chem Biol. 2008 Nov 24;15(11):1156-65. doi: 10.1016/j.chembiol.2008.09.010. PubMed PMID: 19022176.

2: Kallio P, Sultana A, Niemi J, Mäntsälä P, Schneider G. Crystal structure of the polyketide cyclase AknH with bound substrate and product analogue: implications for catalytic mechanism and product stereoselectivity. J Mol Biol. 2006 Mar 17;357(1):210-20. Epub 2006 Jan 6. PubMed PMID: 16414075.

3: Lee TS, Khosla C, Tang Y. Engineered biosynthesis of aklanonic acid analogues. J Am Chem Soc. 2005 Sep 7;127(35):12254-62. PubMed PMID: 16131203; PubMed Central PMCID: PMC1343498.

4: 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.

5: 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.

6: Wohlert SE, Wendt-Pienkowski E, Bao W, Hutchinson CR. Production of aromatic minimal polyketides by the daunorubicin polyketide synthase genes reveals the incompatibility of the heterologous DpsY and JadI cyclases. J Nat Prod. 2001 Aug;64(8):1077-80. PubMed PMID: 11520231.

7: Rajgarhia VB, Priestley ND, Strohl WR. The product of dpsC confers starter unit fidelity upon the daunorubicin polyketide synthase of Streptomyces sp. strain C5. Metab Eng. 2001 Jan;3(1):49-63. PubMed PMID: 11162232.

8: Vetrivel KS, Dharmalingam K. Isolation of a chitinase overproducing mutant of Streptomyces peucetius defective in daunorubicin biosynthesis. Can J Microbiol. 2000 Oct;46(10):956-60. PubMed PMID: 11068684.

9: Kantola J, Kunnari T, Hautala A, Hakala J, Ylihonko K, Mäntsälä P. Elucidation of anthracyclinone biosynthesis by stepwise cloning of genes for anthracyclines from three different Streptomyces spp. Microbiology. 2000 Jan;146 ( Pt 1):155-63. PubMed PMID: 10658662.

10: Vollack KU, Härtig E, Körner H, Zumft WG. Multiple transcription factors of the FNR family in denitrifying Pseudomonas stutzeri: characterization of four fnr-like genes, regulatory responses and cognate metabolic processes. Mol Microbiol. 1999 Mar;31(6):1681-94. Erratum in: Mol Microbiol 1999 Jul;33(2):442. PubMed PMID: 10209742.

11: Kendrew SG, Katayama K, Deutsch E, Madduri K, Hutchinson CR. DnrD cyclase involved in the biosynthesis of doxorubicin: purification and characterization of the recombinant enzyme. Biochemistry. 1999 Apr 13;38(15):4794-9. PubMed PMID: 10200167.

12: Lomovskaya N, Doi-Katayama Y, Filippini S, Nastro C, Fonstein L, Gallo M, Colombo AL, Hutchinson CR. The Streptomyces peucetius dpsY and dnrX genes govern early and late steps of daunorubicin and doxorubicin biosynthesis. J Bacteriol. 1998 May;180(9):2379-86. PubMed PMID: 9573189; PubMed Central PMCID: PMC107179.

13: Rajgarhia VB, Strohl WR. Minimal Streptomyces sp. strain C5 daunorubicin polyketide biosynthesis genes required for aklanonic acid biosynthesis. J Bacteriol. 1997 Apr;179(8):2690-6. PubMed PMID: 9098068; PubMed Central PMCID: PMC179019.

14: Madduri K, Hutchinson CR. Functional characterization and transcriptional analysis of a gene cluster governing early and late steps in daunorubicin biosynthesis in Streptomyces peucetius. J Bacteriol. 1995 Jul;177(13):3879-84. PubMed PMID: 7601857; PubMed Central PMCID: PMC177111.

15: Dickens ML, Ye J, Strohl WR. Analysis of clustered genes encoding both early and late steps in daunomycin biosynthesis by Streptomyces sp. strain C5. J Bacteriol. 1995 Feb;177(3):536-43. PubMed PMID: 7836284; PubMed Central PMCID: PMC176625.

16: Grimm A, Madduri K, Ali A, Hutchinson CR. Characterization of the Streptomyces peucetius ATCC 29050 genes encoding doxorubicin polyketide synthase. Gene. 1994 Dec 30;151(1-2):1-10. PubMed PMID: 7828855.

17: Ylihonko K, Hakala J, Niemi J, Lundell J, Mäntsälä P. Isolation and characterization of aclacinomycin A-non-producing Streptomyces galilaeus (ATCC 31615) mutants. Microbiology. 1994 Jun;140 ( Pt 6):1359-65. PubMed PMID: 8081501.

18: Strohl WR, Connors NC. Significance of anthraquinone formation resulting from the cloning of actinorhodin genes in heterologous streptomycetes. Mol Microbiol. 1992 Jan;6(2):147-52. Review. PubMed PMID: 1545701.

19: Schlegel B, Stengel C, Schumann G, Prauser H, Eckardt K. Aklanonic acid-producing mutants of Streptomyces galilaeus and Streptomyces peucetius var. caesius. J Basic Microbiol. 1987;27(2):107-11. PubMed PMID: 3477632.

20: Schumann G, Stengel C, Eckardt K, Ihn W. Biotransformation of aklanonic acid by blocked mutants of anthracycline-producing strains of Streptomyces galilaeus and Streptomyces peucetius. J Basic Microbiol. 1986;26(4):249-55. PubMed PMID: 3464736.