Epithienamycin D
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| Category | Antibiotics |
| Catalog number | BBF-03188 |
| CAS | 65322-98-7 |
| Molecular Weight | 312.34 |
| Molecular Formula | C13H16N2O5S |
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Description
Epithienamycin D is a carbapenem antibiotic produced by Streptomyces flavogriseus MA-4434 and MB-4638. It has anti-gram-positive bacteria and anti-gram-negative bacteria activity.
Specification
| Synonyms | carbapenem MM22383; MM22383 |
| IUPAC Name | (5R,6S)-3-{[(E)-2-acetamidovinyl]sulfanyl}-6-[(1S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid |
| Canonical SMILES | CC(C1C2CC(=C(N2C1=O)C(=O)O)SC=CNC(=O)C)O |
| InChI | InChI=1S/C13H16N2O5S/c1-6(16)10-8-5-9(21-4-3-14-7(2)17)11(13(19)20)15(8)12(10)18/h3-4,6,8,10,16H,5H2,1-2H3,(H,14,17)(H,19,20)/b4-3+/t6-,8+,10+/m0/s1 |
| InChI Key | PRPNUZWHFGSGRV-RZFSBTTISA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 604.4±55.0°C at 760 mmHg |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Recent developments in carbapenems
Giovanni Bonfiglio, Giovanni Russo, Giuseppe Nicoletti Expert Opin Investig Drugs. 2002 Apr;11(4):529-44. doi: 10.1517/13543784.11.4.529.
Carbapenems are beta-lactam antibiotics characterised by the presence of a beta-lactam ring with a carbon instead of sulfone in the 4-position of the thyazolidinic moiety. The first carbapenem to be utilised in therapy was imipenem, the N-formimidoyl derivative of thienamycin. Imipenem is coadministered with cilastatin, an inhibitor of human renal dehydropeptidase I, as imipenem is hydrolysed by this enzyme. Meropenem was the first carbapenem with a 1-beta-methyl group and 2-thio pyrrolidinyl moiety, which renders this antibiotic stable to renal dehydropeptidase I. Other carbapenems for parenteral administration later discovered include biapenem, panipenem, ertapenem, lenapenem, E-1010, S-4661 and BMS-181139. Carbapenems which are orally administered include sanfetrinem, DZ-2640, CS-834 and GV-129606. Carbapenems have an ultra-broad spectrum of antibacterial activity and stability to almost all clinically relevant beta-lactamases. This differentiates them from all other currently available classes of beta-lactam antibiotics. However, Class B beta-lactamases, along with some rare Class A and D enzymes, are able to hydrolyse these antibiotics. Although Class B enzymes are generally chromosomally-encoded (isolated from Stenotrophomonas maltophilia, Aeromonas spp., Bacillus cereus, Bacteroides fragilis, Flavobacterium spp. and Legionella gormanii), plasmid-metallo-beta-lactamases now are appearing in B. fragilis, Pseudomonas aeruginosa, Acinetobacter baumannii and members of Enterobacteriaceae such as Serratia marcescens and Klebsiella pneumoniae. The number of these enzymes compared to the number of other beta-lactamase types is still low, however, it is likely that they will spread due to the increased selective pressure of carbapenem use. The very broad spectrum of antimicrobial activity associated with a good clinical efficacy and a favourable safety profile makes the carbapenems valuable as 'first-line' antibiotics in initial empirical therapy for the treatment of severe infections.
2. Synthesis of Thienamycin methyl ester from 2-deoxy-D-ribose via Kinugasa reaction
Magdalena Soluch, Barbara Grzeszczyk, Olga Staszewska-Krajewska, Marek Chmielewski, Bartłomiej Furman J Antibiot (Tokyo). 2016 Mar;69(3):164-8. doi: 10.1038/ja.2015.108. Epub 2015 Oct 28.
A novel synthesis of thienamycin is described. The crucial step of the synthesis is based on Cu(I)-mediated Kinugasa cycloaddition/rearrangement cascade reaction between terminal acetylene derived from D-lactic acid and suitable, partially protected, five-membered cyclic nitrone obtained from 2-deoxy-D-ribose. The reaction was performed in the presence of tetramethylguanidine as a base to provide 5,6-trans substituted carbapenam as the main product. Thus obtained carbapenam 11 with (5R,6S) configuration at the azetidinone ring was subsequently subjected to oxidation/deprotection/oxidation reaction sequence to afford the β-keto ester 20, which was directly transformed into N,O-protected methyl ester of thienamycin.
3. Formal synthesis of Thienamycin
Michał Pieczykolan, Bartłomiej Furman, Marek Chmielewski J Antibiot (Tokyo). 2017 Jun;70(6):781-787. doi: 10.1038/ja.2017.44. Epub 2017 Apr 5.
A formal synthesis of Thienamycin from ethyl (E)-crotonate and a cyclic five-membered nitrone derived from 2-deoxy-d-ribose is described. The synthesis involves 1,3-dipolar cycloaddition, cleavage of the N-O bond in the adduct, and intramolecular N-acylation to afford a bicyclic carbapenam skeleton. Subsequent transformations of the five-membered ring substituents provide the title compound.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
