青黴素×耐酸×耐酶

	耐酸	耐酶
C6側鏈特徵	拉電子基	立體障礙
原理	避免側鏈羰基上O的孤對電子會作為親核基攻擊β-lactam	防止β-lactam被β-lactamase開環
①	X	X
②	O	X
③	O	O
④	O	X
⑤	X	X
⑥	X	X

Penicillins (PCN)

• ①②：天然PCN
  • ①：Pencillin G
  • ②：Penicillin V
• ③：β-lactamase-resistant-PCN
• ④：amino-PCN
• ⑤⑥：anti-Pseudomonal-PCN
  • ⑤：carboxy-PCN
  • ⑥：ureido-PCN

Penicillin degradation

補充：以下反應式未必正確，僅供參考。

PCN與酸反應

1. penicillin to penicillenic acid
   
2. penicillenic acid cyclization to penillic acid
   
3. penicillenic acid (lactone) hydrolysis to penamaldic acid
   
4. penamaldic acid reduction: alkene to alkane intermediate
   
5. penamaldic acid oxidation-1: alkane intermediate to alcohol intermediate and penicillamine
   
6. penamaldic acid oxidation-2: alcohol intermediate to penaldic acid
   
7. penaldic acid decarboxylation to penicilloaldehyde
   

PCN與鹼/β-lactamase反應

1. penicillin (lactone) hydrolysis to penicilloic acid
   
2. penicilloic acid decarboxylation to penilloic acid
   

參考資料：

ChemDoodle Web Components | Demos > 2D Sketcher

Foye's Principles of Medicinal Chemistry 7th

[PDF] Penicillin G ’ s function , metabolites , allergy , and resistance | Semantic Scholar

Lactone Hydrolysis

Oxidation of alcohols I: Mechanism and oxidation states | Organic chemistry | Khan Academy

10 - LPS

Decarboxylation Reaction Mechanism of Carboxylic Acids