| 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
-
penicillin to penicillenic acid
-
penicillenic acid cyclization to penillic acid
-
penicillenic acid (lactone) hydrolysis to penamaldic acid
-
penamaldic acid reduction: alkene to alkane intermediate
-
penamaldic acid oxidation-1: alkane intermediate to alcohol intermediate and penicillamine
-
penamaldic acid oxidation-2: alcohol intermediate to penaldic acid
-
penaldic acid decarboxylation to penicilloaldehyde
PCN與鹼/β-lactamase反應
-
penicillin (lactone) hydrolysis to penicilloic acid
-
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
Oxidation of alcohols I: Mechanism and oxidation states | Organic chemistry | Khan Academy
