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Streptolydigin (Molecule of the Month for April 2011)



Streptolydigin is an antibiotic which works by blocking nucleic acid chain elongation by binding to the polymerase, thus stopping RNA polymerase activity inside a cell. Specifically, it inhibits the assembly of the RNA polymerase II transcription complex and DNA polymerase III transcription. It is active against a number of gram positive bacteria.

The term "antibiotic" was coined by Selman Waksman in 1942 to describe any substance produced by a microorganism that is antagonistic to the growth of other microorganisms in high dilution.This definition excluded substances that kill bacteria but are not produced by microorganisms (such as gastric juices and hydrogen peroxide). It also excluded synthetic antibacterial compounds such as the sulfonamides. Many antibacterial compounds are relatively small molecules with a molecular weight of less than 2000 atomic mass units.

With advances in medicinal chemistry, most of today's antibacterials chemically are semisynthetic modifications of various natural compounds. These include, for example, the beta-lactam antibacterials, which include the penicillins (produced by fungi in the genus 'Penicillium'), the cephalosporins, and the carbapenems. Compounds that are still isolated from living organisms are the aminoglycosides, whereas other antibacterials—for example, the sulfonamides, the quinolones, and the oxazolidinones—are produced solely by chemical synthesis.

Formal Chemical Name (IUPAC)
2-[4-[6-(1,6-dimethylspiro[8,9-dioxabicyclo[3.3.1]non-3-ene-2,2'-oxirane]-7 -yl)-4-methylhepta-2,4-dienoyl]-5-hydroxy-1-(5-hydroxy-6-methyloxan-2-yl)-3 -oxo-2H-pyrrol-2-yl]-N-methylpropanamide

References

http://en.wikipedia.org/wiki/Streptolydigin

http://en.wikipedia.org/wiki/Antibiotic

Picture of Streptolydigin

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Streptolydigin structure
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Picture of Streptolydigin

C32 H4 4N2 O9



Update by Karl Harrison
(Molecule of the Month for April 2011 )