Deacetylcephalosporin C | CAS#1476-46-6 | antibiotic

MedKoo Cat#: 581538 | Name: Deacetylcephalosporin C

Description:

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

Deacetylcephalosporin C is antibiotic, it is a compound that undergoes hydroxylation at the C-7 position by the enzyme OCDAC hydroxylase, which requires oxygen, iron, ascorbate, and 2-ketoglutarate as a cosubstrate.

Chemical Structure

Deacetylcephalosporin C

CAS#1476-46-6 (free acid)

Theoretical Analysis

MedKoo Cat#: 581538

Name: Deacetylcephalosporin C

CAS#: 1476-46-6 (free acid)

Chemical Formula: C14H19N3O7S

Exact Mass: 373.0944

Molecular Weight: 373.38

Elemental Analysis: C, 45.04; H, 5.13; N, 11.25; O, 29.99; S, 8.59

Price and Availability

This product was removed for the commercial reasons.

Related CAS #

1476-46-6 (free acid) 26924-64-1 (x sodium) 14488-15-4 (sodium)

Synonym

Antibiotic SF 1623C; Antibiotic WS 3442E; DCPC; Deacetylcephalosporin C; Desacetylcephalosporin C;

IUPAC/Chemical Name

(6R,7R)-7-((R)-5-amino-5-carboxypentanamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

InChi Key

XWCFYHBHOFBVIV-JWKOBGCHSA-N

InChi Code

InChI=1S/C14H19N3O7S/c15-7(13(21)22)2-1-3-8(19)16-9-11(20)17-10(14(23)24)6(4-18)5-25-12(9)17/h7,9,12,18H,1-5,15H2,(H,16,19)(H,21,22)(H,23,24)/t7-,9-,12-/m1/s1

SMILES Code

N[C@@H](C(O)=O)CCCC(N[C@H]1[C@H]2SCC(CO)=C(C(O)=O)N2C1=O)=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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 373.38 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.

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: 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. 2: Cao YX, Lu H, Qiao B, Chen Y, Yuan YJ. Comparison of the secondary metabolites in two scales of cephalosporin C (CPC) fermentation and two different post-treatment processes. J Ind Microbiol Biotechnol. 2013 Jan;40(1):95-103. doi: 10.1007/s10295-012-1203-0. Epub 2012 Oct 9. PubMed PMID: 23053347. 3: 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. 4: 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. 5: 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. 6: Ullán RV, Teijeira F, Martín JF. Expression of the Acremonium chrysogenum cefT gene in Penicillum chrysogenum indicates that it encodes an hydrophilic beta-lactam transporter. Curr Genet. 2008 Sep;54(3):153-61. doi: 10.1007/s00294-008-0207-9. Epub 2008 Jul 31. PubMed PMID: 18668246. 7: Lejon S, Ellis J, Valegård K. The last step in cephalosporin C formation revealed: crystal structures of deacetylcephalosporin C acetyltransferase from Acremonium chrysogenum in complexes with reaction intermediates. J Mol Biol. 2008 Mar 28;377(3):935-44. doi: 10.1016/j.jmb.2008.01.047. Epub 2008 Jan 30. PubMed PMID: 18279889. 8: Ullán RV, Campoy S, Casqueiro J, Fernández FJ, Martín JF. Deacetylcephalosporin C production in Penicillium chrysogenum by expression of the isopenicillin N epimerization, ring expansion, and acetylation genes. Chem Biol. 2007 Mar;14(3):329-39. PubMed PMID: 17379148. 9: 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. 10: Basch J, Franceschini T, Tonzi S, Chiang SJ. Expression of a cephalosporin C esterase gene in Acremonium chrysogenum for the direct production of deacetylcephalosporin C. J Ind Microbiol Biotechnol. 2004 Dec;31(11):531-9. Epub 2004 Nov 13. PubMed PMID: 15672283. 11: Ullán RV, Casqueiro J, Naranjo L, Vaca I, Martín JF. Expression of cefD2 and the conversion of isopenicillin N into penicillin N by the two-component epimerase system are rate-limiting steps in cephalosporin biosynthesis. Mol Genet Genomics. 2004 Dec;272(5):562-70. Epub 2004 Nov 18. PubMed PMID: 15668772. 12: Rodríguez-Sáiz M, Lembo M, Bertetti L, Muraca R, Velasco J, Malcangi A, de la Fuente JL, Barredo JL. Strain improvement for cephalosporin production by Acremonium chrysogenum using geneticin as a suitable transformation marker. FEMS Microbiol Lett. 2004 Jun 1;235(1):43-9. PubMed PMID: 15158260. 13: Lloyd MD, Lipscomb SJ, Hewitson KS, Hensgens CM, Baldwin JE, Schofield CJ. Controlling the substrate selectivity of deacetoxycephalosporin/deacetylcephalosporin C synthase. J Biol Chem. 2004 Apr 9;279(15):15420-6. Epub 2004 Jan 20. PubMed PMID: 14734549. 14: Chin HS, Sim J, Seah KI, Sim TS. Deacetoxycephalosporin C synthase isozymes exhibit diverse catalytic activity and substrate specificity. FEMS Microbiol Lett. 2003 Jan 28;218(2):251-7. PubMed PMID: 12586400. 15: Velasco J, Gutiérrez S, Casqueiro J, Fierro F, Campoy S, Martín JF. Cloning and characterization of the gene cahB encoding a cephalosporin C acetylhydrolase from Acremonium chrysogenum. Appl Microbiol Biotechnol. 2001 Oct;57(3):350-6. PubMed PMID: 11759684. 16: Hamilton CS, Yasuhara A, Baldwin JE, Lloyd MD, Rutledge PJ. Contrasting fates for 6-alpha-methylpenicillin N upon oxidation by deacetoxycephalosporin C synthase (DAOCS) and deacetoxy/deacetylcephalosporin C synthase (DAOC/DACS). Bioorg Med Chem Lett. 2001 Sep 17;11(18):2511-4. PubMed PMID: 11549458. 17: Min W, Begley TP, Myllyharju J, Kivirikko KI. Mechanistic Studies on Prolyl-4-Hydroxylase: Demonstration That the Ferryl Intermediate Does Not Exchange with Water. Bioorg Chem. 2000 Oct;28(5):261-265. PubMed PMID: 11133144. 18: Velasco J, Gutierrez S, Campoy S, Martin JF. Molecular characterization of the Acremonium chrysogenum cefG gene product: the native deacetylcephalosporin C acetyltransferase is not processed into subunits. Biochem J. 1999 Feb 1;337 ( Pt 3):379-85. PubMed PMID: 9895280; PubMed Central PMCID: PMC1219988. 19: Gutiérrez S, Velasco J, Marcos AT, Fernández FJ, Fierro F, Barredo JL, Díez B, Martín JF. Expression of the cefG gene is limiting for cephalosporin biosynthesis in Acremonium chrysogenum. Appl Microbiol Biotechnol. 1997 Nov;48(5):606-14. PubMed PMID: 9421924. 20: Díez B, Mellado E, Fouces R, Rodríguez M, Barredo JL. Recombinant Acremonium chrysogenum strains for the industrial production of cephalosporin. Microbiologia. 1996 Sep;12(3):359-70. Review. PubMed PMID: 8897416.