MedKoo Cat#: 592378 | Name: Aklanonic acid

Description:

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

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

Chemical Structure

Aklanonic acid
CAS#91432-47-2

Theoretical Analysis

MedKoo Cat#: 592378

Name: Aklanonic acid

CAS#: 91432-47-2

Chemical Formula: C21H16O8

Exact Mass: 396.0845

Molecular Weight: 396.35

Elemental Analysis: C, 63.64; H, 4.07; O, 32.29

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 #
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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

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
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.