Synonym
Cephabacin M6; Cephabacin M(sub 6);
IUPAC/Chemical Name
7-(5-amino-5-carboxypentanamido)-3-(24-amino-6-(2-amino-2-oxoethyl)-12,18-bis(3-aminopropyl)-5-hydroxy-21-(hydroxymethyl)-9,15-diisopropyl-3,8,11,14,17,20,23-heptaoxo-2-oxa-7,10,13,16,19,22-hexaazapentacosyl)-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChi Key
FGXDXPRKJSRQLP-UHFFFAOYSA-N
InChi Code
InChI=1S/C47H79N13O18S/c1-21(2)34(57-38(67)26(11-8-14-48)53-40(69)29(18-61)56-37(66)23(5)50)41(70)54-27(12-9-15-49)39(68)58-35(22(3)4)42(71)55-28(16-31(52)63)30(62)17-33(65)78-19-24-20-79-46-47(77-6,45(76)60(46)36(24)44(74)75)59-32(64)13-7-10-25(51)43(72)73/h21-23,25-30,34-35,46,61-62H,7-20,48-51H2,1-6H3,(H2,52,63)(H,53,69)(H,54,70)(H,55,71)(H,56,66)(H,57,67)(H,58,68)(H,59,64)(H,72,73)(H,74,75)
SMILES Code
COC1(C2SCC(COC(CC(C(NC(C(C(C)C)NC(C(NC(C(C(C)C)NC(C(NC(C(NC(C(N)C)=O)CO)=O)CCCN)=O)=O)CCCN)=O)=O)CC(N)=O)O)=O)=C(C(O)=O)N2C1=O)NC(CCCC(C(O)=O)N)=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
1,146.28
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: Nozaki Y, Okonogi K, Katayama N, Ono H, Harada S, Kondo M, Okazaki H. Cephabacins, new cephem antibiotics of bacterial origin. IV. Antibacterial activities, stability to beta-lactamases and mode of action. J Antibiot (Tokyo). 1984 Dec;37(12):1555-65. PubMed PMID: 6335505.
2: Nozaki Y, Katayama N, Tsubotani S, Ono H, Okazaki H. Cephabacin M1-6, new 7-methoxycephem antibiotics of bacterial origin. I. A producing organism, fermentation, biological activities, and mode of action. J Antibiot (Tokyo). 1985 Sep;38(9):1141-51. PubMed PMID: 3905734.
3: Lee JS, Vladimirova MG, Demirev AV, Kim BG, Lim SK, Nam DH. Expression and characterization of polyketide synthase module involved in the late step of cephabacin biosynthesis from Lysobacter lactamgenus. J Microbiol Biotechnol. 2008 Mar;18(3):427-33. PubMed PMID: 18388458.
4: Tsubotani S, Hida T, Ono H, Harada S. Cephabacin M1-6, new 7-methoxycephem antibiotics of bacterial origin. II. Isolation, characterization and structural determination. J Antibiot (Tokyo). 1985 Sep;38(9):1152-65. PubMed PMID: 4066500.
5: Demirev AV, Lee CH, Jaishy BP, Nam DH, Ryu DD. Substrate specificity of nonribosomal peptide synthetase modules responsible for the biosynthesis of the oligopeptide moiety of cephabacin in Lysobacter lactamgenus. FEMS Microbiol Lett. 2006 Feb;255(1):121-8. PubMed PMID: 16436071.
6: Liras P. Biosynthesis and molecular genetics of cephamycins. Cephamycins produced by actinomycetes. Antonie Van Leeuwenhoek. 1999 Jan-Feb;75(1-2):109-24. Review. PubMed PMID: 10422584.
7: Tsubotani S, Hida T, Kasahara F, Wada Y, Harada S. Cephabacins, new cephem antibiotics of bacterial origin. III. Structural determination. J Antibiot (Tokyo). 1984 Dec;37(12):1546-54. PubMed PMID: 6526724.
8: Sohn YS, Nam DH, Ryu DD. Biosynthetic pathway of cephabacins in Lysobacter lactamgenus: molecular and biochemical characterization of the upstream region of the gene clusters for engineering of novel antibiotics. Metab Eng. 2001 Oct;3(4):380-92. PubMed PMID: 11676571.
9: Palissa H, von Döhren H, Kleinkauf H, Ting HH, Baldwin JE. Beta-lactam biosynthesis in a gram-negative eubacterium: purification and characterization of isopenicillin N synthase from Flavobacterium sp. strain SC 12.154. J Bacteriol. 1989 Oct;171(10):5720-8. PubMed PMID: 2793834; PubMed Central PMCID: PMC210420.
