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BFI: Chemistry > Beta-Lactams > Flashcards

Beta-Lactams Flashcards

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1
Q

Beta-lactam antibiotics include…

A

cephalosporins, penicillin derivatives, mono-bantams, carbapenems

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2
Q

Penicillin is produced by?

A

Penicillium spp. including Penicillium chrysogenum

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3
Q

What is the core-structure of penicillin?

A

B-lactam ring + Thiazolide (5-membered) ring

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4
Q

Who discovered Penicillin?

A

Alexander Fleming (1920s-1940s)

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5
Q

What is highly distorted and why?

A

Beta-lactam (endocyclic) amide

N = sp3 (usually sp2) hybridisation; making it susceptible to Nucleophilic attack by water

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6
Q

What is nucleophilic substitution reaction responsible for ? Give an example?

A

Immunotoxicity

An example is development of an allergy - Host proteins participate in a nucleophilic reaction

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7
Q

How did isolated penicillins become active antibacterials?

A

Adding phenyl acetic acid/phenoxyacetic acid to the fermentation broth, 2 potent analogues Penicillin G/V with potent activity

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8
Q

How is 6-APA (-aminopenicillanic acid) made?

A

Deacylation of the side chain in Penicillin G/V using E-coli acylase

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9
Q

Common features in Penicillin analogue

A

B-lactam
Carboxylic acid
Stereochemistry @ dipeptide chain

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10
Q

Cephalosporins produced by…

A

Cephalosporium spp. + Strepmyces spp.

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11
Q

What is the core structure of Cephalosporins?

A

B-lactam ring + Dihydrothiazine (6-membered) ring

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12
Q

What is Cephalosporin C isolated from?

A

Cephalosporin acremonium

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13
Q

What did Cephalosporin C show?

A

Limited antibacterial activity

Resistant to Penicillinase

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14
Q

What does deacylation of Cephalosporin C produce?

A

7-ACA (7-Aminocephalsporanic acid)

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15
Q

Common features of 7-ACA?

A

B-lactam ring
Stereochemistry
Carboxylic acid - acidic group
Leaving group - side chain

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16
Q

What are Transpeptidases?

A

Penicillin-binding proteins
Responsible for the final stages of Peptidoglycan Biosynthesis + target of B-lactams = mediate cross-linking which gives cell wall mechanical strength

17
Q

How many different classes of Transpeptidases?

A

5

18
Q

What are Transpeptidaes made up of?

A

Lysine and Serine

19
Q

What does Penicillin + PBP make?

A

Inactive-acyl-PBP

20
Q

Common features of carbapenems

A

4,5- fused rings
Endocyclic alkenic bond
No amide group @ C6
Unique stereo-chemistry

21
Q

Last line of defence of beta-lactam antibiotics

A

Carbapenems

22
Q

Beta-lactamase resistance to carbapenems

A

Carbapenem-resistance enterobacteriaceae

BFI: Chemistry (3 decks)

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