Deacetoxycephalosporin C (TFA)
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MedKoo CAT#: 581368

CAS#: 26924-74-3 (free acid)

Description: Deacetoxycephalosporin C, also known as DAOC, is an antibiotic and a precursor of cephalosporins excreted by Cephalosporium and Streptomyces species.

Chemical Structure

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Deacetoxycephalosporin C (TFA)
CAS# 26924-74-3 (free acid)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 581368
Name: Deacetoxycephalosporin C (TFA)
CAS#: 26924-74-3 (free acid)
Chemical Formula: C20H22F9N3O12S
Exact Mass: 0.00
Molecular Weight: 699.080
Elemental Analysis: C, 34.34; H, 3.17; F, 24.45; N, 6.01; O, 27.45; S, 4.58

Price and Availability

Size Price Availability Quantity
1mg USD 190 Ready to ship
5mg USD 750 Ready to ship
10mg USD 1250 Ready to ship
25mg USD 2250 Ready to ship
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Related CAS #: 60939-20-0 (sodium)   26924-74-3 (free acid)   55601-34-8 (disodium)   74970-32-4 (x sodium)   49845-68-3    

Synonym: DAOC TFA; Antibiotic WS 3442A TFA; De(acetoxy)cephalosporin C TFA; Deacetoxycephalosporin C Trifluoroacetic acid.

IUPAC/Chemical Name: (6R,7R)-7-((R)-5-amino-5-carboxypentanamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tris(trifluoroacetic acid)

InChi Key: ZTYBAECWWATESB-FOLCZSLLSA-N

InChi Code: InChI=1S/C14H19N3O6S.3C2HF3O2/c1-6-5-24-12-9(11(19)17(12)10(6)14(22)23)16-8(18)4-2-3-7(15)13(20)21;3*3-2(4,5)1(6)7/h7,9,12H,2-5,15H2,1H3,(H,16,18)(H,20,21)(H,22,23);3*(H,6,7)/t7-,9-,12-;;;/m1.../s1

SMILES Code: O=C(C(N12)=C(C)CS[C@]2([H])[C@H](NC(CCC[C@@H](N)C(O)=O)=O)C1=O)O.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F

Appearance: White to off-white solid powder

Purity: >97% (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: 2934.99.9001

More Info:

Biological target: TBD
In vitro activity: TBD
In vivo activity: TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 699.08 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: TBD
In vitro protocol: TBD
In vivo protocol: TBD

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1: Fan K, Lin B, Tao Y, Yang K. Engineering deacetoxycephalosporin C synthase as a catalyst for the bioconversion of penicillins. J Ind Microbiol Biotechnol. 2017 May;44(4-5):705-710. doi: 10.1007/s10295-016-1857-0. Epub 2016 Nov 8. Review. PubMed PMID: 27826726.

2: Wu L, Fan K, Ji J, Yang K. [Evaluation of penicillin expandase mutants and complex substrate inhibition characteristics at high concentrations of penicillin G]. Sheng Wu Gong Cheng Xue Bao. 2015 Dec;31(12):1690-9. Chinese. PubMed PMID: 27093832.

3: Balakrishnan N, Ganesan S, Rajasekaran P, Rajendran L, Teddu S, Durairaaj M. Modified Deacetylcephalosporin C Synthase for the Biotransformation of Semisynthetic Cephalosporins. Appl Environ Microbiol. 2016 Jun 13;82(13):3711-3720. doi: 10.1128/AEM.00174-16. Print 2016 Jul 1. PubMed PMID: 27084018; PubMed Central PMCID: PMC4907206.

4: Lin B, Fan K, Zhao J, Ji J, Wu L, Yang K, Tao Y. Reconstitution of TCA cycle with DAOCS to engineer Escherichia coli into an efficient whole cell catalyst of penicillin G. Proc Natl Acad Sci U S A. 2015 Aug 11;112(32):9855-9. doi: 10.1073/pnas.1502866112. Epub 2015 Jul 27. PubMed PMID: 26216972; PubMed Central PMCID: PMC4538657.

5: Tarhonskaya H, Szöllössi A, Leung IK, Bush JT, Henry L, Chowdhury R, Iqbal A, Claridge TD, Schofield CJ, Flashman E. Studies on deacetoxycephalosporin C synthase support a consensus mechanism for 2-oxoglutarate dependent oxygenases. Biochemistry. 2014 Apr 22;53(15):2483-93. doi: 10.1021/bi500086p. Epub 2014 Apr 11. PubMed PMID: 24684493.

6: Ji J, Fan K, Tian X, Zhang X, Zhang Y, Yang K. Iterative combinatorial mutagenesis as an effective strategy for generation of deacetoxycephalosporin C synthase with improved activity toward penicillin G. Appl Environ Microbiol. 2012 Nov;78(21):7809-12. doi: 10.1128/AEM.02122-12. Epub 2012 Aug 24. PubMed PMID: 22923414; PubMed Central PMCID: PMC3485735.

7: Ji J, Tian X, Fan K, Yang K. New strategy of site-directed mutagenesis identifies new sites to improve Streptomyces clavuligerus deacetoxycephalosporin C synthase activity toward penicillin G. Appl Microbiol Biotechnol. 2012 Mar;93(6):2395-401. doi: 10.1007/s00253-011-3566-y. Epub 2011 Sep 10. PubMed PMID: 21909691.

8: An Y, Dong H, Liu G. Expression of cefF significantly decreased deacetoxycephalosporin C formation during cephalosporin C production in Acremonium chrysogenum. J Ind Microbiol Biotechnol. 2012 Feb;39(2):269-74. doi: 10.1007/s10295-011-1025-5. Epub 2011 Aug 25. PubMed PMID: 21866341.

9: Wu XB, Tian XY, Ji JJ, Wu WB, Fan KQ, Yang KQ. Saturation mutagenesis of Acremonium chrysogenum deacetoxy/deacetylcephalosporin C synthase R308 site confirms its role in controlling substrate specificity. Biotechnol Lett. 2011 Apr;33(4):805-12. doi: 10.1007/s10529-010-0504-5. Epub 2010 Dec 29. PubMed PMID: 21190060.

10: Goo KS, Sim TS. Designing new β-lactams: implications from their targets, resistance factors and synthesizing enzymes. Curr Comput Aided Drug Des. 2011 Mar;7(1):53-80. Review. PubMed PMID: 20883204.

11: Liras P, Demain AL. Chapter 16. Enzymology of beta-lactam compounds with cephem structure produced by actinomycete. Methods Enzymol. 2009;458:401-29. doi: 10.1016/S0076-6879(09)04816-2. PubMed PMID: 19374992.

12: Goo KS, Chua CS, Sim TS. Directed evolution and rational approaches to improving Streptomyces clavuligerus deacetoxycephalosporin C synthase for cephalosporin production. J Ind Microbiol Biotechnol. 2009 May;36(5):619-33. doi: 10.1007/s10295-009-0549-4. Epub 2009 Mar 7. Review. PubMed PMID: 19277744.

13: Goo KS, Chua CS, Sim TS. Relevant double mutations in bioengineered Streptomyces clavuligerus deacetoxycephalosporin C synthase result in higher binding specificities which improve penicillin bioconversion. Appl Environ Microbiol. 2008 Feb;74(4):1167-75. Epub 2007 Dec 14. PubMed PMID: 18083859; PubMed Central PMCID: PMC2258576.

14: Sim Goo K, Song Chua C, Sim TS. A complete library of amino acid alterations at R306 in Streptomyces clavuligerus deacetoxycephalosporin C synthase demonstrates its structural role in the ring-expansion activity. Proteins. 2008 Feb 15;70(3):739-47. PubMed PMID: 17729280.

15: Stok JE, Baldwin JE. Development of enzyme-linked immunosorbent assays for the detection of deacetoxycephalosporin C and isopenicillin N synthase activity. Anal Chim Acta. 2006 Sep 8;577(2):153-62. Epub 2006 Jun 27. PubMed PMID: 17723666.

16: Dreyer J, Eichhorn H, Friedlin E, Kürnsteiner H, Kück U. A homologue of the Aspergillus velvet gene regulates both cephalosporin C biosynthesis and hyphal fragmentation in Acremonium chrysogenum. Appl Environ Microbiol. 2007 May;73(10):3412-22. Epub 2007 Mar 30. PubMed PMID: 17400783; PubMed Central PMCID: PMC1907097.

17: Wei CL, Yang YB, Deng CH, Liu WC, Hsu JS, Lin YC, Liaw SH, Tsai YC. Directed evolution of Streptomyces clavuligerus deacetoxycephalosporin C synthase for enhancement of penicillin G expansion. Appl Environ Microbiol. 2005 Dec;71(12):8873-80. PubMed PMID: 16332884; PubMed Central PMCID: PMC1317366.

18: Wu XB, Fan KQ, Wang QH, Yang KQ. C-terminus mutations of Acremonium chrysogenum deacetoxy/deacetylcephalosporin C synthase with improved activity toward penicillin analogs. FEMS Microbiol Lett. 2005 May 1;246(1):103-10. PubMed PMID: 15869968.

19: Hsu JS, Yang YB, Deng CH, Wei CL, Liaw SH, Tsai YC. Family shuffling of expandase genes to enhance substrate specificity for penicillin G. Appl Environ Microbiol. 2004 Oct;70(10):6257-63. PubMed PMID: 15466573; PubMed Central PMCID: PMC522083.

20: Oster LM, van Scheltinga AC, Valegård K, Hose AM, Dubus A, Hajdu J, Andersson I. Conformational flexibility of the C terminus with implications for substrate binding and catalysis revealed in a new crystal form of deacetoxycephalosporin C synthase. J Mol Biol. 2004 Oct 8;343(1):157-71. PubMed PMID: 15381427.