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Chapter 15 : γ-Lactams and Derivatives

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Abstract:

The β-lactams represent the largest clinical class of antibiotics. Interest has since turned to the pentacycles, which possess certain affinities for penicillin-binding proteins (PBP), such as the γ-lactams, pyrazolidinones, and isoxazolidinones (lactivicin). The first γ-lactams molecules to exhibit antibacterial activity were described in 1986. The first derivative, derivative A, is active against . The opening of the γ-lactam ring is dependent on the substituent at C-3. The increase in lipophilicity of the substituent at C-3 or on the oxime residue enhanced the activity against gram-positive bacteria but decreased that against gram-negative bacteria. Lactivicin is an antibacterial agent isolated from the fermentation of YK-258 and YK-422. Lactivicin is an acidic antibiotic that is soluble in water. The physicochemical properties of lactivicin and the methylated esters of the carboxyl group are summarized. Lactivicin is active against gram-positive bacteria and inactive against gram-negative bacteria. The mechanism of action of lactivicin is similar to that of the β-lactams. Synthetic derivatives have been prepared to reduce the parenteral toxicity and to increase the activity and antibacterial spectrum. The acute toxicity is 400 mg/kg of body weight subcutaneously and more than 400 mg/kg orally. The lack of the γ-lactam nucleus suppresses the antibacterial activity. Derivatives with a D-phenylglycyl group are inactive because they are unstable in a neutral or basic medium.

Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15

Key Concept Ranking

Antibacterial Agents
1.3515241
Gram-Positive Bacteria
1.1429096
Gram-Negative Bacteria
1.0213236
Klebsiella pneumoniae
0.875
1.3515241
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
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References

/content/book/10.1128/9781555815929.ch15
1. Billot-Klein D,, Gutimann L,, Collatz E,, Van Heijenoort J, 1992, Analysis of peptidoglycan precursors of vancomycin-resistant enterococci, Antimicrob Agents Chemother, 36, 14871490.
2. Courvalin P, 1990, Resistance of enterococci to glycopeptides, Antimicrob Agents Chemother, 34, 22912296.
3. Duncan K,, van Heijenoort J,, Walsh CT, 1990, Purification and characterization of the d-alanyl-d-alanine-adding enzyme from Escherichia coli, Biochemistry, 29, 23792386.
4. Gardner AD, 1940, Morphological effects of penicillin on bacteria, Nature, 3713, 837838.
5. Labischinski H,, Barnickel G,, Naumann D,, Ronspeck W,, Bradaczek H, 1985, Conformational studies on the bacterial cell wall peptide analog phenylacetyl d-alanyl d-alanine: comparison between conformations of cell wall peptide analog and those of penicillin G, Biopolymers, 24, 20872112.
6. Malhotra KT,, Nicholas RA, 1992, Substitution of lysine 213 with arginine in penicillin binding protein 5 of Escherichia coli abolishes d-alanine carboxypeptidase activity without affecting penicillin binding, J Biol Chem, 267, 1138611391.
7. Waxman DJ,, Strominger JL, 1982, β-Lactam antibiotics: biochemical modes of action, in Morin RB,, Gorman M, ed, Chemistry and Biology of β-Lactam Antibiotics, vol 3, Academic Press, New York.
8. Wright GD,, Molinas C,, Arthur M,, Courvalin P,, Walsh CT, 1992, Characterization of VanY, a dd-carboxypeptidase from vancomycin-resistant Enterococcus faecium BM4147, Antimicrob Agents Chemother, 36, 15141518.

Tables

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Table 1

Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
Generic image for table
Table 2

Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
Generic image for table
Table 3

Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
Generic image for table
Table 4

Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
Generic image for table
Table 5

Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
Generic image for table
Table 6

Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15
Generic image for table
Table 7

Citation: Bryskier A. 2005. γ-Lactams and Derivatives, p 447-452. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch15

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