Lecture 14 - CH 310 N T Th 2-3:30 LECTURE 14 Textbook...

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1 CH 310 N T Th 2-3:30 LECTURE 14 Textbook Assignment: Chapter 17 (begin) Homework (for credit): POW 7 posted Today’s Topics: Derivatives of Carboxylic Acids Notice & Announcements: Organic Lecture Series 2 Functional Functional Derivatives of Derivatives of Carboxylic Acids Carboxylic Acids Organic Lecture Series 3 • The functional group of an ester is an acyl group bonded to -OR or -OAr – name the alkyl or aryl group bonded to oxygen followed by the name of the acid – change the suffix -ic acid ic acid to -ate ate O O EtO O OEt O O O Ethyl ethanoate (Ethyl acetate) Diethyl butanedioate (Diethyl succinate) Is op ropyl benzoate Esters
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2 Organic Lecture Series 4 • Cyclic esters are called lactones – name the parent carboxylic acid, drop the suffix -ic acid ic acid and add -olactone olactone 4-Butanolactone -Butyrolactone) 3-Butanolactone -Butyrolactone) γ β α β α O O O O H 3 C 2 3 1 2 1 34 6-Hexanolactone -Caprolactone) ε δ γ β α O O 2 1 3 4 56 Esters Organic Lecture Series 5 • The functional group of an amide is an acyl group bonded to a nitrogen atom – IUPAC: drop - oic acid oic acid from the name of the parent acid and add -amide amide – if the amide nitrogen is bonded to an alkyl or aryl group, name the group and show its location on nitrogen by N - CH 3 CNH 2 O 3 C-N H 3 O H-C-N 3 3 O N- Methylacetamide (a 2° amide) Acetamide (a 1° amide) N,N- Dimethyl- formamide (DMF) (a 3° amide) Amides Amides Organic Lecture Series 6 • Cyclic amides are called lactams lactams – name the parent carboxylic acid, drop the suffix -ic acid ic acid and add -lactam lactam α β γ δ ε 6-Hexanolactam -Caprolactam) α β H 3 C O NH O 1 2 1 2 3 4 5 6 3 3-Butanolactam -Butyrolactam) Amides Amides penam –old term for β -lactam
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3 Organic Lecture Series 7 Penicillins the penicillins are a family of β -lactam antibiotics Inhibit cell wall synthesis by acylating and de-activating the required enzymes. The compound is an exceptional “acylating” agent because of the ring strain of the lactam. Organic Lecture Series 8 Penicillins Penicillins the penicillins are a family of β -lactam antibiotics NH H 2 N H H HO N S COOH O Amoxicillin (a β -lactam antibiotic) The penicillins differ in the group bonded to the acyl carbon β -lactam O Organic Lecture Series 9 Cephalosporins Cephalosporins the cephalosporins are also β -lactam antibiotics N S Me O O N H NH 2 H H The cephalosporins differ in the group bonded to the acyl carbon and the side chain of the thiazine ring Cep halexin (Keflex) β -lactam Bacteria develop resistance by producing β -lactamases- enzymes, which can hydrolyze the lactam before it can inhibit cell wall synthesis.
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4 Organic Lecture Series 10 Meropenem Highly resistant to degradation by beta-lactamases or cephalosporinases.
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This note was uploaded on 12/08/2008 for the course BIO 365R taught by Professor Draper during the Fall '08 term at University of Texas at Austin.

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Lecture 14 - CH 310 N T Th 2-3:30 LECTURE 14 Textbook...

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