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Regulation and compartmentalization of β-lactam biosynthesis.

Martín JF, Ullán RV, García-Estrada C - Microb Biotechnol (2009)

Bottom Line: Similarly, the Acremonium two-component CefD1-CefD2 epimerization system is also located in microbodies.This compartmentalization implies intracellular transport of isopenicillin N (in the penicillin pathway) or isopenicillin N and penicillin N in the cephalosporin route.Two transporters of the MFS family cefT and cefM are involved in transport of intermediates and/or secretion of cephalosporins.

View Article: PubMed Central - PubMed

Affiliation: Institute of Biotechnology of León, Science Park, Avda. Real 1, 24006 León, Spain. jf.martin@unileon.es

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Chemical structure of the β‐lactam ring, the penicillins (penam nucleus) and cephalosporins (cephem nucleus). Different penicillins contain distinct hydrophobic or hydrophilic side‐chains (R). The R1 and R2 groups of cephalosporins or cephamycins are indicated below the structure of cephalosporin.
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f1: Chemical structure of the β‐lactam ring, the penicillins (penam nucleus) and cephalosporins (cephem nucleus). Different penicillins contain distinct hydrophobic or hydrophilic side‐chains (R). The R1 and R2 groups of cephalosporins or cephamycins are indicated below the structure of cephalosporin.

Mentions: β‐Lactams, like many other secondary metabolites, have unusual chemical structures. All β‐lactams contain a four‐membered β‐lactam ring closed by an amide bond (Fig. 1). Penicillins contain a bicyclic ‘penam’ nucleus formed by fused β‐lactam and thiazolidine rings and an acyl side‐chain bound to the amino group at C‐6. They are produced by a few Penicillium and Aspergillus species (Aharonowitz et al., 1992). Recently penicillins have been found to be produced by a few other deuteromycetes (Laich et al., 1999; 2002; 2003). A second β‐lactam compound, cephalosporin C, produced by the fungi Acremonium chrysogenum, Paecilomyces persicinus and Kallichroma tethys (Kim et al., 2003) and some other deuteromycetes, contains the cephem nucleus (a six‐membered dihydrothiazine ring fused to the β‐lactam ring) (Fig. 1). Cephalosporin C has a d‐α‐aminoadipyl side‐chain attached to the C‐7 amino group, which is identical to that of hydrophilic penicillin N but differs from those of hydrophobic penicillins. Penicillins and cephalosporins are of great clinical interest as inhibitors of peptidoglycan biosynthesis in bacteria.


Regulation and compartmentalization of β-lactam biosynthesis.

Martín JF, Ullán RV, García-Estrada C - Microb Biotechnol (2009)

Chemical structure of the β‐lactam ring, the penicillins (penam nucleus) and cephalosporins (cephem nucleus). Different penicillins contain distinct hydrophobic or hydrophilic side‐chains (R). The R1 and R2 groups of cephalosporins or cephamycins are indicated below the structure of cephalosporin.
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3815371&req=5

f1: Chemical structure of the β‐lactam ring, the penicillins (penam nucleus) and cephalosporins (cephem nucleus). Different penicillins contain distinct hydrophobic or hydrophilic side‐chains (R). The R1 and R2 groups of cephalosporins or cephamycins are indicated below the structure of cephalosporin.
Mentions: β‐Lactams, like many other secondary metabolites, have unusual chemical structures. All β‐lactams contain a four‐membered β‐lactam ring closed by an amide bond (Fig. 1). Penicillins contain a bicyclic ‘penam’ nucleus formed by fused β‐lactam and thiazolidine rings and an acyl side‐chain bound to the amino group at C‐6. They are produced by a few Penicillium and Aspergillus species (Aharonowitz et al., 1992). Recently penicillins have been found to be produced by a few other deuteromycetes (Laich et al., 1999; 2002; 2003). A second β‐lactam compound, cephalosporin C, produced by the fungi Acremonium chrysogenum, Paecilomyces persicinus and Kallichroma tethys (Kim et al., 2003) and some other deuteromycetes, contains the cephem nucleus (a six‐membered dihydrothiazine ring fused to the β‐lactam ring) (Fig. 1). Cephalosporin C has a d‐α‐aminoadipyl side‐chain attached to the C‐7 amino group, which is identical to that of hydrophilic penicillin N but differs from those of hydrophobic penicillins. Penicillins and cephalosporins are of great clinical interest as inhibitors of peptidoglycan biosynthesis in bacteria.

Bottom Line: Similarly, the Acremonium two-component CefD1-CefD2 epimerization system is also located in microbodies.This compartmentalization implies intracellular transport of isopenicillin N (in the penicillin pathway) or isopenicillin N and penicillin N in the cephalosporin route.Two transporters of the MFS family cefT and cefM are involved in transport of intermediates and/or secretion of cephalosporins.

View Article: PubMed Central - PubMed

Affiliation: Institute of Biotechnology of León, Science Park, Avda. Real 1, 24006 León, Spain. jf.martin@unileon.es

Show MeSH
Related in: MedlinePlus