Brainscape's Knowledge GenomeTM

Browse over 1 million classes created by top students, professors, publishers, and experts.


See full index

BFI: Chemistry > Beta-Lactams > Flashcards

Beta-Lactams Flashcards

You may prefer our related Brainscape-certified flashcards:
Chemistry 101 flashcards AP® Chemistry flashcards Periodic Table flashcards Organic Chemistry 101 flashcards
1
Q

Beta-lactam antibiotics include…

A

cephalosporins, penicillin derivatives, mono-bantams, carbapenems

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

Penicillin is produced by?

A

Penicillium spp. including Penicillium chrysogenum

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

What is the core-structure of penicillin?

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

Who discovered Penicillin?

A

Alexander Fleming (1920s-1940s)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

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

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

Common features in Penicillin analogue

A

B-lactam
Carboxylic acid
Stereochemistry @ dipeptide chain

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

Cephalosporins produced by…

A

Cephalosporium spp. + Strepmyces spp.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

What is the core structure of Cephalosporins?

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

What is Cephalosporin C isolated from?

A

Cephalosporin acremonium

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

What did Cephalosporin C show?

A

Limited antibacterial activity

Resistant to Penicillinase

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

What does deacylation of Cephalosporin C produce?

A

7-ACA (7-Aminocephalsporanic acid)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

Common features of 7-ACA?

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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)

Brainscape helps you reach your goals faster, through stronger study habits.
© 2024 Bold Learning Solutions. Terms and Conditions