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𝐻 − 𝑂 − 𝐶 − 𝑅1
𝑂
𝐻 − 𝑂 − 𝐶 − 𝑅2
𝑂
𝐻 − 𝑂 − 𝐶 − 𝑅3
𝑂
𝐶𝐻2 − 𝑂𝐻
𝐶𝐻 − 𝑂𝐻
𝐶𝐻2 − 𝑂𝐻
3𝐻2𝑂 ↑
𝐻2𝐶 − 𝑂 − 𝐶 − 𝑅1
𝑂
𝐻𝐶 − 𝑂 − 𝐶 − 𝑅2
𝑂
𝐻2𝐶 − 𝑂 − 𝐶 − 𝑅3
𝑂
−𝐶 − 𝐶 − 𝐶 − 𝐶 − 𝐶 − 𝐶 − 𝑂𝐻
𝑂
𝜷 𝜶
𝑪𝒂𝒓𝒃𝒐𝒏𝒚𝒍 𝒈𝒓𝒐𝒖𝒑
𝐵𝑜𝑛𝑑 𝑖𝑠 𝑏𝑟𝑜𝑘𝑒𝑛
𝑎𝑡 𝛽 − 𝐶𝑎𝑟𝑏𝑜𝑛
𝑆ℎ𝑜𝑟𝑡𝑒𝑟 𝐹𝑎𝑡𝑡𝑦 𝑎𝑐𝑖𝑑 + 𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨
𝑅 − 𝐶𝐻2𝐶𝐻2 − 𝐶𝑂𝑂−
𝜷 𝜶
𝑭𝒂𝒕𝒕𝒚 𝑨𝒄𝒊𝒅
𝑅 − 𝐶𝐻2𝐶𝐻2 − 𝐶 −
𝜷 𝜶
𝑨𝒄𝒚𝒍 𝒂𝒅𝒆𝒏𝒚𝒍𝒂𝒕𝒆
𝑨𝑴𝑷
𝐴𝑐𝑦𝑙 𝐶𝑜𝐴
𝑆𝑦𝑛𝑡ℎ𝑎𝑠𝑒
𝑨𝑻𝑷 𝑷𝑷𝒊 𝑂
𝑅 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶 −
𝜷 𝜶
𝑺 − 𝑪𝒐𝑨
𝑂
𝑨𝒄𝒚𝒍 𝑪𝒐𝑨
𝑷𝑷𝒊
𝟐𝑷𝒊
𝑃𝑦𝑟𝑜 −
𝑝ℎ𝑜𝑠𝑝ℎ𝑎𝑡𝑎𝑠𝑒
• 𝐼𝑛𝑛𝑒𝑟 𝑚𝑖𝑡𝑜𝑐ℎ𝑜𝑛𝑑𝑟𝑖𝑎𝑙 𝑚𝑒𝑚𝑏𝑟𝑎𝑛𝑒 𝑖𝑠 𝑖𝑚𝑝𝑒𝑟𝑚𝑒𝑎𝑏𝑙𝑒 𝑡𝑜
𝐴𝑐𝑦𝑙 𝐶𝑜𝐴. 𝐻𝑒𝑛𝑐𝑒, 𝑪𝒂𝒓𝒏𝒊𝒕𝒊𝒏𝒆 𝒔𝒉𝒖𝒕𝒕𝒍𝒆 𝒔𝒚𝒔𝒕𝒆𝒎 𝑖𝑠 𝑝𝑟𝑒𝑠𝑒𝑛𝑡.
𝑅 − 𝐶 − 𝑆𝐶𝑜𝐴
𝑂
𝑨𝒄𝒚𝒍 𝑪𝒐𝑨
𝑅 − 𝐶 − 𝑆𝐶𝑜𝐴
𝑂
𝑨𝒄𝒚𝒍 𝑪𝒐𝑨
𝑰𝒏𝒏𝒆𝒓
𝒎𝒆𝒎𝒃.
𝑪𝒂𝒓𝒏𝒊𝒕𝒊𝒏𝒆
𝑅 − 𝐶 −
𝑂
𝑨𝒄𝒚𝒍 𝑪𝒂𝒓𝒏𝒊𝒕𝒊𝒏𝒆
𝐶𝑎𝑟𝑛. 𝑅 − 𝐶 −
𝑂
𝑨𝒄𝒚𝒍 𝑪𝒂𝒓𝒏𝒊𝒕𝒊𝒏𝒆
𝐶𝑎𝑟𝑛.
𝑪𝒂𝒓𝒏𝒊𝒕𝒊𝒏𝒆
𝑪𝒂𝒓𝒏𝒊𝒕𝒏𝒊𝒏𝒆 𝑨𝒄𝒚𝒍
𝑻𝒓𝒂𝒏𝒔𝒇𝒆𝒓𝒂𝒔𝒆 𝑰
𝑪𝒂𝒓𝒏𝒊𝒕𝒏𝒊𝒏𝒆 𝑨𝒄𝒚𝒍
𝑻𝒓𝒂𝒏𝒔𝒇𝒆𝒓𝒂𝒔𝒆 𝑰𝑰
𝑴
𝑨
𝑻
𝑹
𝑰
𝑿
𝑪
𝒀
𝑻
𝑶
𝑺
𝑶
𝑳
𝑅 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶 −
𝜷 𝜶
𝑺 − 𝑪𝒐𝑨
𝑂
𝑨𝒄𝒚𝒍 𝑪𝒐𝑨
𝑅 − 𝐶𝐻 = 𝐶𝐻 − 𝐶 −
𝜷 𝜶
𝑺 − 𝑪𝒐𝑨
𝑂
𝑻𝒓𝒂𝒏𝒔 − 𝒆𝒏𝒐𝒚𝒍 𝑪𝒐𝑨
𝑭𝑨𝑫
𝑭𝑨𝑫𝑯𝟐
𝑅 − 𝐶𝐻 = 𝐶𝐻 − 𝐶 −
𝜷 𝜶
𝑺 − 𝑪𝒐𝑨
𝑂
𝑻𝒓𝒂𝒏𝒔 − 𝒆𝒏𝒐𝒚𝒍 𝑪𝒐𝑨
𝑯𝟐𝑶
𝑅 − 𝐶𝐻 − 𝐶𝐻 − 𝐶 −
𝜷 𝜶
𝑺 − 𝑪𝒐𝑨
𝑂
𝑂𝐻 𝐻
𝜷 𝑯𝒚𝒅𝒓𝒐𝒙𝒚 𝒂𝒄𝒚𝒍 𝑪𝒐𝑨
𝑅 − 𝐶 − 𝐶𝐻2 − 𝐶 −
𝜷 𝜶
𝑺 − 𝑪𝒐𝑨
𝑂
𝑵𝑨𝑫+
𝑵𝑨𝑫𝑯 + 𝑯+
𝑂𝐻
𝐻
𝜷 𝑯𝒚𝒅𝒓𝒐𝒙𝒚 𝒂𝒄𝒚𝒍 𝑪𝒐𝑨
𝑅 − 𝐶 − 𝐶𝐻2 − 𝐶 −
𝜷 𝜶
𝑺 − 𝑪𝒐𝑨
𝑂
𝑂
𝜷 𝑲𝒆𝒕𝒐 𝒂𝒄𝒚𝒍 𝑪𝒐𝑨
𝑅 − 𝐶 − 𝐶𝐻2 − 𝐶 −
𝜷 𝜶
𝑺 − 𝑪𝒐𝑨
𝑂
𝑂
𝜷 𝑲𝒆𝒕𝒐 𝒂𝒄𝒚𝒍 𝑪𝒐𝑨
𝑅 − 𝐶 − 𝑺𝑪𝒐𝑨
𝑂
𝑨𝒄𝒚𝒍 𝑪𝒐𝑨
𝐶𝐻3 − 𝐶 − 𝑺𝑪𝒐𝑨
𝑂
𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨
𝑪𝒐𝑨𝑺𝑯
(𝟐 𝑪𝒂𝒓𝒃𝒐𝒏 𝒍𝒆𝒔𝒔)
𝐶𝑛 ⋯ ⋯ 𝐶3 − 𝐶2 − 𝐶1 − 𝑺𝑪𝒐𝑨
𝑂
𝐶(𝑛−2) ⋯ ⋯ 𝐶 − 𝐶 − 𝑺𝑪𝒐𝑨
𝑂
𝑪𝒏 𝑨𝒄𝒚𝒍 𝑪𝒐𝑨
𝑪(𝒏−𝟐) 𝑨𝒄𝒚𝒍 𝑪𝒐𝑨
𝜷 − 𝑶𝒙𝒊𝒅𝒂𝒕𝒊𝒐𝒏
𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴
• 𝑹𝒆𝒂𝒄𝒕𝒊𝒐𝒏 𝒇𝒐𝒓 𝟏 𝒓𝒐𝒖𝒏𝒅 𝒐𝒇 𝜷 − 𝑶𝒙𝒊𝒅𝒂𝒕𝒊𝒐𝒏:
𝐶𝑛 𝐴𝑐𝑦𝑙 𝐶𝑜𝐴 + 𝑁𝐴𝐷+ + 𝐹𝐴𝐷 + 𝐻2𝑂 + 𝐶𝑜𝐴𝑆𝐻
𝐶(𝑛−2) 𝐴𝑐𝑦𝑙 𝐶𝑜𝐴 + 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 + 𝑁𝐴𝐷𝐻 + 𝐻+ + 𝐹𝐴𝐷𝐻2
• 1 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 𝑚𝑜𝑙𝑒𝑐𝑢𝑙𝑒 𝑖𝑠 𝑟𝑒𝑙𝑒𝑎𝑠𝑒𝑑 𝑖𝑛 𝑒𝑣𝑒𝑟𝑦 𝑟𝑜𝑢𝑛𝑑 𝑜𝑓
𝛽 − 𝑜𝑥𝑖𝑑𝑎𝑡𝑖𝑜𝑛 𝑒𝑥𝑐𝑒𝑝𝑡 𝑙𝑎𝑠𝑡 𝑜𝑛𝑒 , 𝑤ℎ𝑒𝑟𝑒 2 𝑎𝑟𝑒 𝑓𝑜𝑟𝑚𝑒𝑑.
∴ 𝑻𝒉𝒆 𝒄𝒐𝒎𝒑𝒍𝒆𝒕𝒆 𝒐𝒙𝒊𝒅𝒂𝒕𝒊𝒐𝒏 𝒐𝒄𝒄𝒖𝒓𝒔 𝒊𝒏
𝒏
𝟐
− 𝟏 𝒓𝒐𝒖𝒏𝒅𝒔.
• 𝑶𝒗𝒆𝒓𝒂𝒍𝒍 𝑹𝒆𝒂𝒄𝒕𝒊𝒐𝒏 𝒇𝒐𝒓 𝒏 𝑪𝒂𝒓𝒃𝒐𝒏 𝑭𝒂𝒕𝒕𝒚 𝑨𝒄𝒊𝒅 𝒄𝒉𝒂𝒊𝒏:
𝑨𝒄𝒚𝒍 𝑪𝒐𝑨 [𝑪𝒏] +
𝑛
2
− 1
𝐹𝐴𝐷 + 𝑁𝐴𝐷+
+ 𝐻2𝑂 + 𝐶𝑜𝐴𝑆𝐻
𝒏
𝟐
(𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨) +
𝑛
2
− 1
𝐹𝐴𝐷𝐻2 +
𝑁𝐴𝐷𝐻 + 𝐻+
• 𝑃𝑎𝑙𝑚𝑖𝑡𝑜𝑦𝑙 𝐶𝑜𝐴 𝑖𝑠 𝑎 𝑪𝟏𝟔 𝒇𝒂𝒕𝒕𝒚 𝒂𝒄𝒊𝒅.
• 𝐻𝑒𝑛𝑐𝑒, 𝑖𝑡 𝑤𝑖𝑙𝑙 𝑦𝑖𝑒𝑙𝑑 8 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 𝑚𝑜𝑙𝑒𝑐𝑢𝑙𝑒𝑠 𝑡ℎ𝑟𝑜𝑢𝑔ℎ
7 𝑐𝑦𝑐𝑙𝑒𝑠 𝑜𝑓 𝛽 − 𝑜𝑥𝑖𝑑𝑎𝑡𝑖𝑜𝑛.
𝑷𝒂𝒍𝒎𝒊𝒕𝒐𝒚𝒍 𝑪𝒐𝑨 + 7 [𝐶𝑜𝐴𝑆𝐻 + 𝐻2𝑂 + 𝑁𝐴𝐷+ + 𝐹𝐴𝐷]
𝟖 [𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨] + 7 [𝑁𝐴𝐷𝐻 + 𝐻+
+ 𝐹𝐴𝐷𝐻2]
𝛽 − 𝑂𝑥𝑖𝑑𝑎𝑡𝑖𝑜𝑛
7 𝐶𝑦𝑐𝑙𝑒𝑠
⟶⟶⟶
• 𝐸𝑁𝐸𝑅𝐺𝐸𝑇𝐼𝐶𝑆 •
7 𝑁𝐴𝐷𝐻 = 7 × 2.5 𝐴𝑇𝑃 = 𝟏𝟕. 𝟓 𝑨𝑻𝑷
7 𝐹𝐴𝐷𝐻2 = 7 × 1.5 𝐴𝑇𝑃 = 𝟏𝟎. 𝟓 𝑨𝑻𝑷
8 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 = 8 × 10 𝐴𝑇𝑃 = 𝟖𝟎 𝑨𝑻𝑷 [𝑣𝑖𝑎 𝐾𝑟𝑒𝑏′
𝑠 𝐶𝑦𝑐𝑙𝑒]
𝐴𝑐𝑡𝑖𝑣𝑎𝑡𝑖𝑜𝑛 (𝑢𝑡𝑖𝑙𝑖𝑧𝑒𝑑) = −𝟐 𝑨𝑻𝑷
𝑁𝑒𝑡 𝐴𝑇𝑃 𝐺𝑎𝑖𝑛 = 17.5 + 10.5 + 80 − 2 = 𝟏𝟎𝟔 𝑨𝑻𝑷
𝐶𝐻2 − 𝑂𝐻
𝐶𝐻 − 𝑂𝐻
𝐶𝐻2 − 𝑂𝐻
𝐶𝐻2 − 𝑂𝐻
𝐶𝐻 − 𝑂𝐻
𝐶𝐻2 − 𝑂𝑃𝑂3
2−
𝐶𝐻2 − 𝑂𝐻
𝐶 = 𝑂
𝐶𝐻2 − 𝑂𝑃𝑂3
2−
𝑫𝑯𝑨𝑷
𝑮𝑨𝑷
⇌
𝐺𝑙𝑢𝑐𝑜𝑠𝑒
𝑫𝒊𝒉𝒚𝒅𝒓𝒐𝒙𝒚𝒂𝒄𝒆𝒕𝒐𝒏𝒆
−𝒑𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒆
𝑮𝒍𝒚𝒄𝒆𝒓𝒐𝒍 𝟑 −
𝒑𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒆 𝑮𝑳𝒀𝑪𝑬𝑹𝑶𝑳
• 𝐶𝑖𝑡𝑟𝑎𝑡𝑒 𝑇𝑟𝑎𝑛𝑠𝑝𝑜𝑟𝑡 𝑆𝑦𝑠𝑡𝑒𝑚 •
𝑷𝒚𝒓𝒖𝒗𝒂𝒕𝒆
𝑶𝒙𝒂𝒍𝒐𝒂𝒄𝒆𝒕𝒂𝒕𝒆 𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨
𝑃𝐷𝐻
𝐶𝑜𝑚𝑝𝑙𝑒𝑥
𝑃𝑦𝑟𝑢𝑣𝑎𝑡𝑒
𝐶𝑎𝑟𝑏𝑜𝑥𝑦𝑙𝑎𝑠𝑒
𝑯𝑪𝑶𝟑
−
⟶
⟶ 𝑪𝑶𝟐
𝑪𝒊𝒕𝒓𝒂𝒕𝒆
𝑪𝒊𝒕𝒓𝒂𝒕𝒆
𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨
𝑶𝒙𝒂𝒍𝒐𝒂𝒄𝒆𝒕𝒂𝒕𝒆
𝐶𝑖𝑡𝑟𝑎𝑡𝑒
𝐿𝑦𝑎𝑠𝑒
⟵ 𝑪𝒐𝑨𝑺𝑯
⟵ 𝑨𝑻𝑷
𝑷𝒊 + 𝑨𝑫𝑷 ⟵
𝑴𝒂𝒍𝒂𝒕𝒆
𝑷𝒚𝒓𝒖𝒗𝒂𝒕𝒆
𝑀𝑎𝑙𝑎𝑡𝑒
𝐷𝑒ℎ𝑦𝑑𝑟𝑜𝑔𝑒𝑛𝑎𝑠𝑒
𝑵𝑨𝑫+
⟵
𝑵𝑨𝑫𝑯 ⟶
+𝑯+
𝑴𝑨𝑻𝑹𝑰𝑿
𝑪𝒀𝑻𝑶𝑺𝑶𝑳
𝐶𝐻3 − 𝐶 − 𝑺𝑪𝒐𝑨
𝑂
𝐻𝑂𝑂𝐶 − 𝐶𝐻2 − 𝐶 − 𝑺𝑪𝒐𝑨
𝑂
𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨
𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑪𝒐𝑨
𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴
𝐶𝑎𝑟𝑏𝑜𝑥𝑦𝑙𝑎𝑠𝑒
𝑨𝑻𝑷 𝑨𝑫𝑷 + 𝑷𝒊
𝑯𝑪𝑶𝟑
⊖
• 𝑭𝒂𝒕𝒕𝒚 𝑨𝒄𝒊𝒅 𝑺𝒚𝒏𝒕𝒉𝒂𝒔𝒆 𝑪𝒐𝒎𝒑𝒍𝒆𝒙 𝑐𝑎𝑟𝑟𝑖𝑒𝑠 𝑜𝑢𝑡 𝐹𝑎𝑡𝑡𝑦 𝐴𝑐𝑖𝑑
𝑆𝑦𝑛𝑡ℎ𝑒𝑠𝑖𝑠.
𝑨𝒄𝒚𝒍 𝑪𝒂𝒓𝒓𝒊𝒆𝒓 𝑷𝒓𝒐𝒕𝒆𝒊𝒏
[𝑨𝑪𝑷]
~~~
~~~
⋯ ⋯ ⋯ ⋯ ⋯ ⋯ ⋯ ⋯ 𝑺𝒆𝒓𝒊𝒏𝒆
𝑯 − 𝑺
𝑆𝑢𝑙𝑝ℎ𝑦 − ℎ𝑦𝑑𝑟𝑦𝑙 𝑔𝑟𝑜𝑢𝑝
𝑃𝑟𝑜𝑠𝑡ℎ𝑒𝑡𝑖𝑐 𝑔𝑟𝑜𝑢𝑝
𝑷𝒉𝒐𝒔𝒑𝒉𝒐 −
𝒑𝒂𝒏𝒕𝒆𝒕𝒉𝒆𝒊𝒏𝒆
𝐶𝐻3 − 𝐶 − 𝑺𝑪𝒐𝑨
𝑂
𝐻𝑂𝑂𝐶 − 𝐶𝐻2 − 𝐶 − 𝑺𝑪𝒐𝑨
𝑂
𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨 𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑪𝒐𝑨
𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 − 𝐴𝐶𝑃
𝑇𝑟𝑎𝑛𝑠𝑎𝑐𝑦𝑙𝑎𝑠𝑒
𝑀𝑎𝑙𝑜𝑛𝑦𝑙 𝐶𝑜𝐴 − 𝐴𝐶𝑃
𝑇𝑟𝑎𝑛𝑠𝑎𝑐𝑦𝑙𝑎𝑠𝑒
𝑪𝒐𝑨𝑺𝑯 𝑪𝒐𝑨𝑺𝑯
𝑨𝑪𝑷 − 𝑺𝑯 𝑨𝑪𝑷 − 𝑺𝑯
𝐶𝐻3 − 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
𝐻𝑂𝑂𝐶 − 𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
𝑨𝒄𝒆𝒕𝒚𝒍 𝑨𝑪𝑷 𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑨𝑪𝑷
𝐶𝐻3 − 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
−𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
𝑨𝒄𝒆𝒕𝒚𝒍 𝑨𝑪𝑷 𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑨𝑪𝑷
𝑪
𝑶
𝑶
⊖
𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
𝐶𝐻3 − 𝐶 −
𝑂
𝑨𝒄𝒆𝒕𝒐𝒂𝒄𝒚𝒍 𝑨𝑪𝑷
𝛽 − 𝐾𝑒𝑡𝑜𝑎𝑐𝑦𝑙
𝐴𝐶𝑃 𝑆𝑦𝑛𝑡ℎ𝑎𝑠𝑒
𝐴𝑐𝑦𝑙 − 𝑚𝑎𝑙𝑜𝑛𝑦𝑙 𝐴𝐶𝑃
𝑐𝑜𝑛𝑑𝑒𝑛𝑠𝑖𝑛𝑔 𝑒𝑛𝑧𝑦𝑚𝑒
𝑨𝑪𝑷 − 𝑺𝑯
𝑪𝑶𝟐
𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
𝐶𝐻3 − 𝐶 −
𝑂
𝑨𝒄𝒆𝒕𝒐𝒂𝒄𝒚𝒍 𝑨𝑪𝑷
𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
𝐶𝐻3 − 𝐶𝐻 −
𝑂𝐻
𝟑 − 𝑯𝒚𝒅𝒓𝒐𝒙𝒚𝒃𝒖𝒕𝒚𝒓𝒚𝒍 𝑨𝑪𝑷
𝜷 − 𝑯𝒚𝒅𝒓𝒐𝒙𝒚𝒂𝒄𝒚𝒍 𝑨𝑪𝑷
𝑂𝑅
𝛽 − 𝐾𝑒𝑡𝑜𝑎𝑐𝑦𝑙
𝐴𝐶𝑃 𝑅𝑒𝑑𝑢𝑐𝑡𝑎𝑠𝑒
𝑵𝑨𝑫𝑷+
𝑵𝑨𝑫𝑷𝑯
+𝑯+
𝐾𝑒𝑡𝑜𝑎𝑐𝑦𝑙
𝑔𝑟𝑜𝑢𝑝
𝐻𝑦𝑑𝑟𝑜𝑥𝑦𝑎𝑐𝑦𝑙
𝑔𝑟𝑜𝑢𝑝
𝟑 − 𝑯𝒚𝒅𝒓𝒐𝒙𝒚𝒃𝒖𝒕𝒚𝒓𝒚𝒍 𝑨𝑪𝑷
− 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
𝐶𝐻3 − 𝐶𝐻 −
𝑂𝐻
𝐶𝐻
𝐻
𝐶𝐻3 − 𝐶𝐻 = 𝐶𝐻 − 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
𝑪𝒓𝒐𝒕𝒐𝒏𝒚𝒍 𝑨𝑪𝑷
𝐻𝑦𝑑𝑟𝑜𝑥𝑦𝑎𝑐𝑦𝑙 𝐴𝐶𝑃
𝐷𝑒ℎ𝑦𝑑𝑟𝑎𝑡𝑎𝑠𝑒
𝑯𝟐𝑶
𝐶𝐻3 − 𝐶𝐻 = 𝐶𝐻 − 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
𝑪𝒓𝒐𝒕𝒐𝒏𝒚𝒍 𝑨𝑪𝑷
𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
𝑩𝒖𝒕𝒚𝒓𝒚𝒍 𝑨𝑪𝑷
𝐸𝑛𝑜𝑦𝑙 𝐴𝐶𝑃
𝑅𝑒𝑑𝑢𝑐𝑡𝑎𝑠𝑒
𝑵𝑨𝑫𝑷+
𝑵𝑨𝑫𝑷𝑯
+𝑯+
𝐶𝐻3 − 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
𝑨𝒄𝒆𝒕𝒚𝒍 𝑨𝑪𝑷
𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
𝑩𝒖𝒕𝒚𝒓𝒚𝒍 𝑨𝑪𝑷
𝑀𝑎𝑙𝑜𝑛𝑦𝑙 𝐴𝐶𝑃 ⟶
𝑨𝑪𝑷 − 𝑺𝑯 ⟵
𝑯𝟐𝑶 ⟵
2 − 𝐶𝑎𝑟𝑏𝑜𝑛
𝐶𝑜𝑚𝑝𝑜𝑢𝑛𝑑
4 − 𝐶𝑎𝑟𝑏𝑜𝑛
𝐶𝑜𝑚𝑝𝑜𝑢𝑛𝑑
𝟐 − 𝑪𝒂𝒓𝒃𝒐𝒏 𝒇𝒓𝒂𝒈𝒎𝒆𝒏𝒕
𝒇𝒓𝒐𝒎 𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑪𝒐𝑨
⟶ 𝑪𝑶𝟐
• 𝑬𝒏𝒆𝒓𝒈𝒆𝒕𝒊𝒄𝒔: 𝟐 𝑵𝑨𝑫𝑷𝑯 + 𝟐𝑯+
⟶ 𝟐 𝑵𝑨𝑫𝑷+
𝑺 − 𝑨𝑪𝑷
𝑶
𝑺 − 𝑨𝑪𝑷
𝑶
𝑶
𝑺 − 𝑨𝑪𝑷
𝑶
𝑶
𝑶
𝑺 − 𝑨𝑪𝑷
𝑶
𝑺 − 𝑨𝑪𝑷
𝑶
𝑶𝑯
𝑺 − 𝑨𝑪𝑷
𝑶
𝑪𝒐𝒏𝒅𝒆𝒏𝒔𝒂𝒕𝒊𝒐𝒏
𝑹𝒆𝒅𝒖𝒄𝒕𝒊𝒐𝒏 𝑹𝒆𝒅𝒖𝒄𝒕𝒊𝒐𝒏
𝑫𝒆𝒉𝒚𝒅𝒓𝒂𝒕𝒊𝒐𝒏
𝟐𝒏𝒅
𝑹𝑶𝑼𝑵𝑫
𝑬𝑳𝑶𝑵𝑮𝑨𝑻𝑰𝑶𝑵
𝑪𝒀𝑪𝑳𝑬
①
𝑪𝟐 𝑭𝒂𝒕𝒕𝒚 𝒂𝒄𝒊𝒅
𝑪𝟒 𝑭𝒂𝒕𝒕𝒚 𝒂𝒄𝒊𝒅
𝑺 − 𝑨𝑪𝑷
𝑶
𝑺 − 𝑨𝑪𝑷
𝑶
𝑺 − 𝑨𝑪𝑷
𝑶
𝑺 − 𝑨𝑪𝑷
𝑶
𝟏 𝑪𝒚𝒄𝒍𝒆
𝟐 𝑪𝒚𝒄𝒍𝒆𝒔
𝟕 𝑪𝒚𝒄𝒍𝒆𝒔
𝟐 − 𝑪𝒂𝒓𝒃𝒐𝒏
𝟒 − 𝑪𝒂𝒓𝒃𝒐𝒏
𝟔 − 𝑪𝒂𝒓𝒃𝒐𝒏
𝟏𝟔 − 𝑪𝒂𝒓𝒃𝒐𝒏
𝐶16 ⋯ ⋯ − 𝐶 − 𝐶 − 𝐶 − 𝑺 − 𝑨𝑪𝑷
𝑂
𝐶16 ⋯ ⋯ − 𝐶 − 𝐶 − 𝐶 − 𝑂𝐻
𝑂
𝑇ℎ𝑖𝑜𝑒𝑠𝑡𝑒𝑟𝑎𝑠𝑒
𝐻2𝑂 ⟶
𝑷𝒂𝒍𝒎𝒊𝒕𝒐𝒚𝒍 𝑨𝑪𝑷
𝑷𝒂𝒍𝒎𝒊𝒕𝒂𝒕𝒆
𝐴𝐶𝑃 − 𝑆𝐻
• 1 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 + 7 [𝑀𝑎𝑙𝑜𝑛𝑦𝑙 𝐶𝑜𝐴] ⟶ 𝑃𝑎𝑙𝑚𝑖𝑡𝑎𝑡𝑒
• 7 × 2 𝑁𝐴𝐷𝑃𝐻 + 2𝐻+ ⟶ 7 × [2 𝑁𝐴𝐷𝑃+]
• 8 𝐶𝑜𝐴𝑆𝐻 𝑎𝑟𝑒 𝑟𝑒𝑙𝑒𝑎𝑠𝑒𝑑.
• 7 𝐶𝑂2 𝑎𝑟𝑒 𝑟𝑒𝑙𝑒𝑎𝑠𝑒𝑑 𝑑𝑢𝑒 𝑡𝑜 𝐶𝑜𝑛𝑑𝑒𝑛𝑠𝑎𝑡𝑖𝑜𝑛.
• 7 𝐻2𝑂 𝑎𝑟𝑒 𝑟𝑒𝑙𝑒𝑎𝑠𝑒𝑑 𝑏𝑦 𝐷𝑒ℎ𝑦𝑑𝑟𝑎𝑡𝑖𝑜𝑛.
• 1 𝐻2𝑂 𝑖𝑠 𝑢𝑠𝑒𝑑 𝑓𝑜𝑟 𝐻𝑦𝑑𝑟𝑜𝑙𝑦𝑠𝑖𝑠.
𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨 + 𝟕 𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑪𝒐𝑨 + 14 [𝑁𝐴𝐷𝑃𝐻 + 𝐻+]
𝑷𝒂𝒍𝒎𝒊𝒕𝒂𝒕𝒆 + 8 𝐶𝑜𝐴𝑆𝐻 + 7 𝐶𝑂2 + 6 𝐻2𝑂
+ 14 𝑁𝐴𝐷𝑃+
• 𝑁𝑜𝑤, 1 𝑀𝑎𝑙𝑜𝑛𝑦𝑙 𝐶𝑜𝐴 𝑖𝑠 𝑠𝑦𝑛𝑡ℎ𝑒𝑠𝑖𝑧𝑒𝑑 𝑓𝑟𝑜𝑚 1 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴
𝑎𝑠 𝑓𝑜𝑙𝑙𝑜𝑤𝑠:
𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨 + 𝐴𝑇𝑃 𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑪𝒐𝑨 + 𝐴𝐷𝑃 + 𝑃𝑖
+𝑯𝑪𝑶𝟑
−
𝟖 𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨 + 7 [𝐴𝑇𝑃 + 𝐻𝐶𝑂3
−
] + 14 [𝑁𝐴𝐷𝑃𝐻 + 𝐻+]
𝑷𝒂𝒍𝒎𝒊𝒕𝒂𝒕𝒆 + 8 𝐶𝑜𝐴𝑆𝐻 + 7 𝐶𝑂2 + 6 𝐻2𝑂
+ 7 [𝐴𝐷𝑃 + 𝑃𝑖] + 14 𝑁𝐴𝐷𝑃+
𝐶𝐻2 − 𝑂𝐻
𝐶𝐻 − 𝑂𝐻
𝐶𝐻2 − 𝑂𝐻
𝐶𝐻2 − 𝑂𝐻
𝐶𝐻 − 𝑂𝐻
𝐶𝐻2 − 𝑂𝑃𝑂3
2−
𝐺𝑙𝑦𝑐𝑒𝑟𝑜𝑙
𝐾𝑖𝑛𝑎𝑠𝑒
𝑨𝑻𝑷 𝑨𝑫𝑷
𝑷𝒊
𝑮𝒍𝒚𝒄𝒆𝒓𝒐𝒍 𝟑 −
𝒑𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒆
𝑮𝒍𝒚𝒄𝒆𝒓𝒐𝒍
𝐶𝐻2 −
𝐶𝐻 − 𝑂𝐻
𝐶𝐻2 − 𝑂𝑃𝑂3
2−
𝐺𝑙𝑦𝑐𝑒𝑟𝑜𝑙 3 − 𝑃.
𝐴𝑐𝑦𝑙𝑡𝑟𝑎𝑛𝑠𝑓𝑒𝑟𝑎𝑠𝑒
𝑂 − 𝐶 − 𝑅1
𝑂
𝑭𝑨 − 𝑪𝒐𝑨
𝑪𝒐𝑨𝑺𝑯
𝑳𝒚𝒔𝒐𝒑𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒊𝒅𝒊𝒄 𝒂𝒄𝒊𝒅
𝐶𝐻2 −
𝐶𝐻 − 𝑂𝐻
𝐶𝐻2 − 𝑂𝑃𝑂3
2−
𝑂 − 𝐶 − 𝑅1
𝑂
𝑳𝒚𝒔𝒐𝒑𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒊𝒅𝒊𝒄
𝑨𝒄𝒊𝒅
𝐶𝐻2 −
−𝐶𝐻
𝐶𝐻2 − 𝑂𝑃𝑂3
2−
𝑂 − 𝐶 − 𝑅1
𝑂
𝑷𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒊𝒅𝒊𝒄 𝑨𝒄𝒊𝒅
𝑅2 − 𝐶 − 𝑂
𝑂
𝐴𝑐𝑦𝑙𝑔𝑙𝑦𝑐𝑒𝑟𝑜𝑝ℎ𝑜𝑠𝑝ℎ𝑎𝑡𝑒
𝐴𝑐𝑦𝑙𝑡𝑟𝑎𝑛𝑠𝑓𝑒𝑟𝑎𝑠𝑒
𝐶𝐻2 −
−𝐶𝐻
𝐶𝐻2 − 𝑂𝐻
𝑂 − 𝐶 − 𝑅1
𝑂
𝑷𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒊𝒅𝒊𝒄
𝑨𝒄𝒊𝒅
𝑅2 − 𝐶 − 𝑂
𝑂
𝑫𝒊𝒂𝒄𝒚𝒍𝒈𝒍𝒚𝒄𝒆𝒓𝒐𝒍
𝑻𝒓𝒊𝒂𝒄𝒚𝒍𝒈𝒍𝒚𝒄𝒆𝒓𝒐𝒍
𝐶𝐻2 −
−𝐶𝐻
𝐶𝐻2 −
𝑂 − 𝐶 − 𝑅1
𝑂
𝑅2 − 𝐶 − 𝑂
𝑂
𝑂 − 𝐶 − 𝑅3
𝑂
𝐷𝑖𝑎𝑐𝑦𝑙𝑔𝑙𝑦𝑐𝑒𝑟𝑜𝑙
𝐴𝑐𝑦𝑙𝑡𝑟𝑎𝑛𝑠𝑓𝑒𝑟𝑎𝑠𝑒
𝑭𝑨 − 𝑪𝒐𝑨 ⟶
Lipid Metabolism

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Lipid Metabolism

  • 1. 𝐻 − 𝑂 − 𝐶 − 𝑅1 𝑂 𝐻 − 𝑂 − 𝐶 − 𝑅2 𝑂 𝐻 − 𝑂 − 𝐶 − 𝑅3 𝑂 𝐶𝐻2 − 𝑂𝐻 𝐶𝐻 − 𝑂𝐻 𝐶𝐻2 − 𝑂𝐻 3𝐻2𝑂 ↑ 𝐻2𝐶 − 𝑂 − 𝐶 − 𝑅1 𝑂 𝐻𝐶 − 𝑂 − 𝐶 − 𝑅2 𝑂 𝐻2𝐶 − 𝑂 − 𝐶 − 𝑅3 𝑂
  • 2. −𝐶 − 𝐶 − 𝐶 − 𝐶 − 𝐶 − 𝐶 − 𝑂𝐻 𝑂 𝜷 𝜶 𝑪𝒂𝒓𝒃𝒐𝒏𝒚𝒍 𝒈𝒓𝒐𝒖𝒑 𝐵𝑜𝑛𝑑 𝑖𝑠 𝑏𝑟𝑜𝑘𝑒𝑛 𝑎𝑡 𝛽 − 𝐶𝑎𝑟𝑏𝑜𝑛 𝑆ℎ𝑜𝑟𝑡𝑒𝑟 𝐹𝑎𝑡𝑡𝑦 𝑎𝑐𝑖𝑑 + 𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨
  • 3. 𝑅 − 𝐶𝐻2𝐶𝐻2 − 𝐶𝑂𝑂− 𝜷 𝜶 𝑭𝒂𝒕𝒕𝒚 𝑨𝒄𝒊𝒅 𝑅 − 𝐶𝐻2𝐶𝐻2 − 𝐶 − 𝜷 𝜶 𝑨𝒄𝒚𝒍 𝒂𝒅𝒆𝒏𝒚𝒍𝒂𝒕𝒆 𝑨𝑴𝑷 𝐴𝑐𝑦𝑙 𝐶𝑜𝐴 𝑆𝑦𝑛𝑡ℎ𝑎𝑠𝑒 𝑨𝑻𝑷 𝑷𝑷𝒊 𝑂 𝑅 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶 − 𝜷 𝜶 𝑺 − 𝑪𝒐𝑨 𝑂 𝑨𝒄𝒚𝒍 𝑪𝒐𝑨 𝑷𝑷𝒊 𝟐𝑷𝒊 𝑃𝑦𝑟𝑜 − 𝑝ℎ𝑜𝑠𝑝ℎ𝑎𝑡𝑎𝑠𝑒
  • 4. • 𝐼𝑛𝑛𝑒𝑟 𝑚𝑖𝑡𝑜𝑐ℎ𝑜𝑛𝑑𝑟𝑖𝑎𝑙 𝑚𝑒𝑚𝑏𝑟𝑎𝑛𝑒 𝑖𝑠 𝑖𝑚𝑝𝑒𝑟𝑚𝑒𝑎𝑏𝑙𝑒 𝑡𝑜 𝐴𝑐𝑦𝑙 𝐶𝑜𝐴. 𝐻𝑒𝑛𝑐𝑒, 𝑪𝒂𝒓𝒏𝒊𝒕𝒊𝒏𝒆 𝒔𝒉𝒖𝒕𝒕𝒍𝒆 𝒔𝒚𝒔𝒕𝒆𝒎 𝑖𝑠 𝑝𝑟𝑒𝑠𝑒𝑛𝑡. 𝑅 − 𝐶 − 𝑆𝐶𝑜𝐴 𝑂 𝑨𝒄𝒚𝒍 𝑪𝒐𝑨 𝑅 − 𝐶 − 𝑆𝐶𝑜𝐴 𝑂 𝑨𝒄𝒚𝒍 𝑪𝒐𝑨 𝑰𝒏𝒏𝒆𝒓 𝒎𝒆𝒎𝒃. 𝑪𝒂𝒓𝒏𝒊𝒕𝒊𝒏𝒆 𝑅 − 𝐶 − 𝑂 𝑨𝒄𝒚𝒍 𝑪𝒂𝒓𝒏𝒊𝒕𝒊𝒏𝒆 𝐶𝑎𝑟𝑛. 𝑅 − 𝐶 − 𝑂 𝑨𝒄𝒚𝒍 𝑪𝒂𝒓𝒏𝒊𝒕𝒊𝒏𝒆 𝐶𝑎𝑟𝑛. 𝑪𝒂𝒓𝒏𝒊𝒕𝒊𝒏𝒆 𝑪𝒂𝒓𝒏𝒊𝒕𝒏𝒊𝒏𝒆 𝑨𝒄𝒚𝒍 𝑻𝒓𝒂𝒏𝒔𝒇𝒆𝒓𝒂𝒔𝒆 𝑰 𝑪𝒂𝒓𝒏𝒊𝒕𝒏𝒊𝒏𝒆 𝑨𝒄𝒚𝒍 𝑻𝒓𝒂𝒏𝒔𝒇𝒆𝒓𝒂𝒔𝒆 𝑰𝑰 𝑴 𝑨 𝑻 𝑹 𝑰 𝑿 𝑪 𝒀 𝑻 𝑶 𝑺 𝑶 𝑳
  • 5.
  • 6. 𝑅 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶 − 𝜷 𝜶 𝑺 − 𝑪𝒐𝑨 𝑂 𝑨𝒄𝒚𝒍 𝑪𝒐𝑨 𝑅 − 𝐶𝐻 = 𝐶𝐻 − 𝐶 − 𝜷 𝜶 𝑺 − 𝑪𝒐𝑨 𝑂 𝑻𝒓𝒂𝒏𝒔 − 𝒆𝒏𝒐𝒚𝒍 𝑪𝒐𝑨 𝑭𝑨𝑫 𝑭𝑨𝑫𝑯𝟐
  • 7. 𝑅 − 𝐶𝐻 = 𝐶𝐻 − 𝐶 − 𝜷 𝜶 𝑺 − 𝑪𝒐𝑨 𝑂 𝑻𝒓𝒂𝒏𝒔 − 𝒆𝒏𝒐𝒚𝒍 𝑪𝒐𝑨 𝑯𝟐𝑶 𝑅 − 𝐶𝐻 − 𝐶𝐻 − 𝐶 − 𝜷 𝜶 𝑺 − 𝑪𝒐𝑨 𝑂 𝑂𝐻 𝐻 𝜷 𝑯𝒚𝒅𝒓𝒐𝒙𝒚 𝒂𝒄𝒚𝒍 𝑪𝒐𝑨
  • 8. 𝑅 − 𝐶 − 𝐶𝐻2 − 𝐶 − 𝜷 𝜶 𝑺 − 𝑪𝒐𝑨 𝑂 𝑵𝑨𝑫+ 𝑵𝑨𝑫𝑯 + 𝑯+ 𝑂𝐻 𝐻 𝜷 𝑯𝒚𝒅𝒓𝒐𝒙𝒚 𝒂𝒄𝒚𝒍 𝑪𝒐𝑨 𝑅 − 𝐶 − 𝐶𝐻2 − 𝐶 − 𝜷 𝜶 𝑺 − 𝑪𝒐𝑨 𝑂 𝑂 𝜷 𝑲𝒆𝒕𝒐 𝒂𝒄𝒚𝒍 𝑪𝒐𝑨
  • 9. 𝑅 − 𝐶 − 𝐶𝐻2 − 𝐶 − 𝜷 𝜶 𝑺 − 𝑪𝒐𝑨 𝑂 𝑂 𝜷 𝑲𝒆𝒕𝒐 𝒂𝒄𝒚𝒍 𝑪𝒐𝑨 𝑅 − 𝐶 − 𝑺𝑪𝒐𝑨 𝑂 𝑨𝒄𝒚𝒍 𝑪𝒐𝑨 𝐶𝐻3 − 𝐶 − 𝑺𝑪𝒐𝑨 𝑂 𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨 𝑪𝒐𝑨𝑺𝑯 (𝟐 𝑪𝒂𝒓𝒃𝒐𝒏 𝒍𝒆𝒔𝒔)
  • 10. 𝐶𝑛 ⋯ ⋯ 𝐶3 − 𝐶2 − 𝐶1 − 𝑺𝑪𝒐𝑨 𝑂 𝐶(𝑛−2) ⋯ ⋯ 𝐶 − 𝐶 − 𝑺𝑪𝒐𝑨 𝑂 𝑪𝒏 𝑨𝒄𝒚𝒍 𝑪𝒐𝑨 𝑪(𝒏−𝟐) 𝑨𝒄𝒚𝒍 𝑪𝒐𝑨 𝜷 − 𝑶𝒙𝒊𝒅𝒂𝒕𝒊𝒐𝒏 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴
  • 11. • 𝑹𝒆𝒂𝒄𝒕𝒊𝒐𝒏 𝒇𝒐𝒓 𝟏 𝒓𝒐𝒖𝒏𝒅 𝒐𝒇 𝜷 − 𝑶𝒙𝒊𝒅𝒂𝒕𝒊𝒐𝒏: 𝐶𝑛 𝐴𝑐𝑦𝑙 𝐶𝑜𝐴 + 𝑁𝐴𝐷+ + 𝐹𝐴𝐷 + 𝐻2𝑂 + 𝐶𝑜𝐴𝑆𝐻 𝐶(𝑛−2) 𝐴𝑐𝑦𝑙 𝐶𝑜𝐴 + 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 + 𝑁𝐴𝐷𝐻 + 𝐻+ + 𝐹𝐴𝐷𝐻2 • 1 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 𝑚𝑜𝑙𝑒𝑐𝑢𝑙𝑒 𝑖𝑠 𝑟𝑒𝑙𝑒𝑎𝑠𝑒𝑑 𝑖𝑛 𝑒𝑣𝑒𝑟𝑦 𝑟𝑜𝑢𝑛𝑑 𝑜𝑓 𝛽 − 𝑜𝑥𝑖𝑑𝑎𝑡𝑖𝑜𝑛 𝑒𝑥𝑐𝑒𝑝𝑡 𝑙𝑎𝑠𝑡 𝑜𝑛𝑒 , 𝑤ℎ𝑒𝑟𝑒 2 𝑎𝑟𝑒 𝑓𝑜𝑟𝑚𝑒𝑑. ∴ 𝑻𝒉𝒆 𝒄𝒐𝒎𝒑𝒍𝒆𝒕𝒆 𝒐𝒙𝒊𝒅𝒂𝒕𝒊𝒐𝒏 𝒐𝒄𝒄𝒖𝒓𝒔 𝒊𝒏 𝒏 𝟐 − 𝟏 𝒓𝒐𝒖𝒏𝒅𝒔. • 𝑶𝒗𝒆𝒓𝒂𝒍𝒍 𝑹𝒆𝒂𝒄𝒕𝒊𝒐𝒏 𝒇𝒐𝒓 𝒏 𝑪𝒂𝒓𝒃𝒐𝒏 𝑭𝒂𝒕𝒕𝒚 𝑨𝒄𝒊𝒅 𝒄𝒉𝒂𝒊𝒏: 𝑨𝒄𝒚𝒍 𝑪𝒐𝑨 [𝑪𝒏] + 𝑛 2 − 1 𝐹𝐴𝐷 + 𝑁𝐴𝐷+ + 𝐻2𝑂 + 𝐶𝑜𝐴𝑆𝐻 𝒏 𝟐 (𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨) + 𝑛 2 − 1 𝐹𝐴𝐷𝐻2 + 𝑁𝐴𝐷𝐻 + 𝐻+
  • 12. • 𝑃𝑎𝑙𝑚𝑖𝑡𝑜𝑦𝑙 𝐶𝑜𝐴 𝑖𝑠 𝑎 𝑪𝟏𝟔 𝒇𝒂𝒕𝒕𝒚 𝒂𝒄𝒊𝒅. • 𝐻𝑒𝑛𝑐𝑒, 𝑖𝑡 𝑤𝑖𝑙𝑙 𝑦𝑖𝑒𝑙𝑑 8 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 𝑚𝑜𝑙𝑒𝑐𝑢𝑙𝑒𝑠 𝑡ℎ𝑟𝑜𝑢𝑔ℎ 7 𝑐𝑦𝑐𝑙𝑒𝑠 𝑜𝑓 𝛽 − 𝑜𝑥𝑖𝑑𝑎𝑡𝑖𝑜𝑛. 𝑷𝒂𝒍𝒎𝒊𝒕𝒐𝒚𝒍 𝑪𝒐𝑨 + 7 [𝐶𝑜𝐴𝑆𝐻 + 𝐻2𝑂 + 𝑁𝐴𝐷+ + 𝐹𝐴𝐷] 𝟖 [𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨] + 7 [𝑁𝐴𝐷𝐻 + 𝐻+ + 𝐹𝐴𝐷𝐻2] 𝛽 − 𝑂𝑥𝑖𝑑𝑎𝑡𝑖𝑜𝑛 7 𝐶𝑦𝑐𝑙𝑒𝑠 ⟶⟶⟶ • 𝐸𝑁𝐸𝑅𝐺𝐸𝑇𝐼𝐶𝑆 • 7 𝑁𝐴𝐷𝐻 = 7 × 2.5 𝐴𝑇𝑃 = 𝟏𝟕. 𝟓 𝑨𝑻𝑷 7 𝐹𝐴𝐷𝐻2 = 7 × 1.5 𝐴𝑇𝑃 = 𝟏𝟎. 𝟓 𝑨𝑻𝑷 8 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 = 8 × 10 𝐴𝑇𝑃 = 𝟖𝟎 𝑨𝑻𝑷 [𝑣𝑖𝑎 𝐾𝑟𝑒𝑏′ 𝑠 𝐶𝑦𝑐𝑙𝑒] 𝐴𝑐𝑡𝑖𝑣𝑎𝑡𝑖𝑜𝑛 (𝑢𝑡𝑖𝑙𝑖𝑧𝑒𝑑) = −𝟐 𝑨𝑻𝑷 𝑁𝑒𝑡 𝐴𝑇𝑃 𝐺𝑎𝑖𝑛 = 17.5 + 10.5 + 80 − 2 = 𝟏𝟎𝟔 𝑨𝑻𝑷
  • 13.
  • 14. 𝐶𝐻2 − 𝑂𝐻 𝐶𝐻 − 𝑂𝐻 𝐶𝐻2 − 𝑂𝐻 𝐶𝐻2 − 𝑂𝐻 𝐶𝐻 − 𝑂𝐻 𝐶𝐻2 − 𝑂𝑃𝑂3 2− 𝐶𝐻2 − 𝑂𝐻 𝐶 = 𝑂 𝐶𝐻2 − 𝑂𝑃𝑂3 2− 𝑫𝑯𝑨𝑷 𝑮𝑨𝑷 ⇌ 𝐺𝑙𝑢𝑐𝑜𝑠𝑒 𝑫𝒊𝒉𝒚𝒅𝒓𝒐𝒙𝒚𝒂𝒄𝒆𝒕𝒐𝒏𝒆 −𝒑𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒆 𝑮𝒍𝒚𝒄𝒆𝒓𝒐𝒍 𝟑 − 𝒑𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒆 𝑮𝑳𝒀𝑪𝑬𝑹𝑶𝑳
  • 15.
  • 16. • 𝐶𝑖𝑡𝑟𝑎𝑡𝑒 𝑇𝑟𝑎𝑛𝑠𝑝𝑜𝑟𝑡 𝑆𝑦𝑠𝑡𝑒𝑚 • 𝑷𝒚𝒓𝒖𝒗𝒂𝒕𝒆 𝑶𝒙𝒂𝒍𝒐𝒂𝒄𝒆𝒕𝒂𝒕𝒆 𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨 𝑃𝐷𝐻 𝐶𝑜𝑚𝑝𝑙𝑒𝑥 𝑃𝑦𝑟𝑢𝑣𝑎𝑡𝑒 𝐶𝑎𝑟𝑏𝑜𝑥𝑦𝑙𝑎𝑠𝑒 𝑯𝑪𝑶𝟑 − ⟶ ⟶ 𝑪𝑶𝟐 𝑪𝒊𝒕𝒓𝒂𝒕𝒆 𝑪𝒊𝒕𝒓𝒂𝒕𝒆 𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨 𝑶𝒙𝒂𝒍𝒐𝒂𝒄𝒆𝒕𝒂𝒕𝒆 𝐶𝑖𝑡𝑟𝑎𝑡𝑒 𝐿𝑦𝑎𝑠𝑒 ⟵ 𝑪𝒐𝑨𝑺𝑯 ⟵ 𝑨𝑻𝑷 𝑷𝒊 + 𝑨𝑫𝑷 ⟵ 𝑴𝒂𝒍𝒂𝒕𝒆 𝑷𝒚𝒓𝒖𝒗𝒂𝒕𝒆 𝑀𝑎𝑙𝑎𝑡𝑒 𝐷𝑒ℎ𝑦𝑑𝑟𝑜𝑔𝑒𝑛𝑎𝑠𝑒 𝑵𝑨𝑫+ ⟵ 𝑵𝑨𝑫𝑯 ⟶ +𝑯+ 𝑴𝑨𝑻𝑹𝑰𝑿 𝑪𝒀𝑻𝑶𝑺𝑶𝑳
  • 17. 𝐶𝐻3 − 𝐶 − 𝑺𝑪𝒐𝑨 𝑂 𝐻𝑂𝑂𝐶 − 𝐶𝐻2 − 𝐶 − 𝑺𝑪𝒐𝑨 𝑂 𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨 𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑪𝒐𝑨 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 𝐶𝑎𝑟𝑏𝑜𝑥𝑦𝑙𝑎𝑠𝑒 𝑨𝑻𝑷 𝑨𝑫𝑷 + 𝑷𝒊 𝑯𝑪𝑶𝟑 ⊖
  • 18. • 𝑭𝒂𝒕𝒕𝒚 𝑨𝒄𝒊𝒅 𝑺𝒚𝒏𝒕𝒉𝒂𝒔𝒆 𝑪𝒐𝒎𝒑𝒍𝒆𝒙 𝑐𝑎𝑟𝑟𝑖𝑒𝑠 𝑜𝑢𝑡 𝐹𝑎𝑡𝑡𝑦 𝐴𝑐𝑖𝑑 𝑆𝑦𝑛𝑡ℎ𝑒𝑠𝑖𝑠. 𝑨𝒄𝒚𝒍 𝑪𝒂𝒓𝒓𝒊𝒆𝒓 𝑷𝒓𝒐𝒕𝒆𝒊𝒏 [𝑨𝑪𝑷] ~~~ ~~~ ⋯ ⋯ ⋯ ⋯ ⋯ ⋯ ⋯ ⋯ 𝑺𝒆𝒓𝒊𝒏𝒆 𝑯 − 𝑺 𝑆𝑢𝑙𝑝ℎ𝑦 − ℎ𝑦𝑑𝑟𝑦𝑙 𝑔𝑟𝑜𝑢𝑝 𝑃𝑟𝑜𝑠𝑡ℎ𝑒𝑡𝑖𝑐 𝑔𝑟𝑜𝑢𝑝 𝑷𝒉𝒐𝒔𝒑𝒉𝒐 − 𝒑𝒂𝒏𝒕𝒆𝒕𝒉𝒆𝒊𝒏𝒆
  • 19. 𝐶𝐻3 − 𝐶 − 𝑺𝑪𝒐𝑨 𝑂 𝐻𝑂𝑂𝐶 − 𝐶𝐻2 − 𝐶 − 𝑺𝑪𝒐𝑨 𝑂 𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨 𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑪𝒐𝑨 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 − 𝐴𝐶𝑃 𝑇𝑟𝑎𝑛𝑠𝑎𝑐𝑦𝑙𝑎𝑠𝑒 𝑀𝑎𝑙𝑜𝑛𝑦𝑙 𝐶𝑜𝐴 − 𝐴𝐶𝑃 𝑇𝑟𝑎𝑛𝑠𝑎𝑐𝑦𝑙𝑎𝑠𝑒 𝑪𝒐𝑨𝑺𝑯 𝑪𝒐𝑨𝑺𝑯 𝑨𝑪𝑷 − 𝑺𝑯 𝑨𝑪𝑷 − 𝑺𝑯 𝐶𝐻3 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 𝐻𝑂𝑂𝐶 − 𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 𝑨𝒄𝒆𝒕𝒚𝒍 𝑨𝑪𝑷 𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑨𝑪𝑷
  • 20. 𝐶𝐻3 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 −𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 𝑨𝒄𝒆𝒕𝒚𝒍 𝑨𝑪𝑷 𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑨𝑪𝑷 𝑪 𝑶 𝑶 ⊖ 𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 𝐶𝐻3 − 𝐶 − 𝑂 𝑨𝒄𝒆𝒕𝒐𝒂𝒄𝒚𝒍 𝑨𝑪𝑷 𝛽 − 𝐾𝑒𝑡𝑜𝑎𝑐𝑦𝑙 𝐴𝐶𝑃 𝑆𝑦𝑛𝑡ℎ𝑎𝑠𝑒 𝐴𝑐𝑦𝑙 − 𝑚𝑎𝑙𝑜𝑛𝑦𝑙 𝐴𝐶𝑃 𝑐𝑜𝑛𝑑𝑒𝑛𝑠𝑖𝑛𝑔 𝑒𝑛𝑧𝑦𝑚𝑒 𝑨𝑪𝑷 − 𝑺𝑯 𝑪𝑶𝟐
  • 21. 𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 𝐶𝐻3 − 𝐶 − 𝑂 𝑨𝒄𝒆𝒕𝒐𝒂𝒄𝒚𝒍 𝑨𝑪𝑷 𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 𝐶𝐻3 − 𝐶𝐻 − 𝑂𝐻 𝟑 − 𝑯𝒚𝒅𝒓𝒐𝒙𝒚𝒃𝒖𝒕𝒚𝒓𝒚𝒍 𝑨𝑪𝑷 𝜷 − 𝑯𝒚𝒅𝒓𝒐𝒙𝒚𝒂𝒄𝒚𝒍 𝑨𝑪𝑷 𝑂𝑅 𝛽 − 𝐾𝑒𝑡𝑜𝑎𝑐𝑦𝑙 𝐴𝐶𝑃 𝑅𝑒𝑑𝑢𝑐𝑡𝑎𝑠𝑒 𝑵𝑨𝑫𝑷+ 𝑵𝑨𝑫𝑷𝑯 +𝑯+ 𝐾𝑒𝑡𝑜𝑎𝑐𝑦𝑙 𝑔𝑟𝑜𝑢𝑝 𝐻𝑦𝑑𝑟𝑜𝑥𝑦𝑎𝑐𝑦𝑙 𝑔𝑟𝑜𝑢𝑝
  • 22. 𝟑 − 𝑯𝒚𝒅𝒓𝒐𝒙𝒚𝒃𝒖𝒕𝒚𝒓𝒚𝒍 𝑨𝑪𝑷 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 𝐶𝐻3 − 𝐶𝐻 − 𝑂𝐻 𝐶𝐻 𝐻 𝐶𝐻3 − 𝐶𝐻 = 𝐶𝐻 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 𝑪𝒓𝒐𝒕𝒐𝒏𝒚𝒍 𝑨𝑪𝑷 𝐻𝑦𝑑𝑟𝑜𝑥𝑦𝑎𝑐𝑦𝑙 𝐴𝐶𝑃 𝐷𝑒ℎ𝑦𝑑𝑟𝑎𝑡𝑎𝑠𝑒 𝑯𝟐𝑶
  • 23. 𝐶𝐻3 − 𝐶𝐻 = 𝐶𝐻 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 𝑪𝒓𝒐𝒕𝒐𝒏𝒚𝒍 𝑨𝑪𝑷 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 𝑩𝒖𝒕𝒚𝒓𝒚𝒍 𝑨𝑪𝑷 𝐸𝑛𝑜𝑦𝑙 𝐴𝐶𝑃 𝑅𝑒𝑑𝑢𝑐𝑡𝑎𝑠𝑒 𝑵𝑨𝑫𝑷+ 𝑵𝑨𝑫𝑷𝑯 +𝑯+
  • 24. 𝐶𝐻3 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 𝑨𝒄𝒆𝒕𝒚𝒍 𝑨𝑪𝑷 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 𝑩𝒖𝒕𝒚𝒓𝒚𝒍 𝑨𝑪𝑷 𝑀𝑎𝑙𝑜𝑛𝑦𝑙 𝐴𝐶𝑃 ⟶ 𝑨𝑪𝑷 − 𝑺𝑯 ⟵ 𝑯𝟐𝑶 ⟵ 2 − 𝐶𝑎𝑟𝑏𝑜𝑛 𝐶𝑜𝑚𝑝𝑜𝑢𝑛𝑑 4 − 𝐶𝑎𝑟𝑏𝑜𝑛 𝐶𝑜𝑚𝑝𝑜𝑢𝑛𝑑 𝟐 − 𝑪𝒂𝒓𝒃𝒐𝒏 𝒇𝒓𝒂𝒈𝒎𝒆𝒏𝒕 𝒇𝒓𝒐𝒎 𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑪𝒐𝑨 ⟶ 𝑪𝑶𝟐 • 𝑬𝒏𝒆𝒓𝒈𝒆𝒕𝒊𝒄𝒔: 𝟐 𝑵𝑨𝑫𝑷𝑯 + 𝟐𝑯+ ⟶ 𝟐 𝑵𝑨𝑫𝑷+
  • 25. 𝑺 − 𝑨𝑪𝑷 𝑶 𝑺 − 𝑨𝑪𝑷 𝑶 𝑶 𝑺 − 𝑨𝑪𝑷 𝑶 𝑶 𝑶 𝑺 − 𝑨𝑪𝑷 𝑶 𝑺 − 𝑨𝑪𝑷 𝑶 𝑶𝑯 𝑺 − 𝑨𝑪𝑷 𝑶 𝑪𝒐𝒏𝒅𝒆𝒏𝒔𝒂𝒕𝒊𝒐𝒏 𝑹𝒆𝒅𝒖𝒄𝒕𝒊𝒐𝒏 𝑹𝒆𝒅𝒖𝒄𝒕𝒊𝒐𝒏 𝑫𝒆𝒉𝒚𝒅𝒓𝒂𝒕𝒊𝒐𝒏 𝟐𝒏𝒅 𝑹𝑶𝑼𝑵𝑫 𝑬𝑳𝑶𝑵𝑮𝑨𝑻𝑰𝑶𝑵 𝑪𝒀𝑪𝑳𝑬 ① 𝑪𝟐 𝑭𝒂𝒕𝒕𝒚 𝒂𝒄𝒊𝒅 𝑪𝟒 𝑭𝒂𝒕𝒕𝒚 𝒂𝒄𝒊𝒅
  • 26. 𝑺 − 𝑨𝑪𝑷 𝑶 𝑺 − 𝑨𝑪𝑷 𝑶 𝑺 − 𝑨𝑪𝑷 𝑶 𝑺 − 𝑨𝑪𝑷 𝑶 𝟏 𝑪𝒚𝒄𝒍𝒆 𝟐 𝑪𝒚𝒄𝒍𝒆𝒔 𝟕 𝑪𝒚𝒄𝒍𝒆𝒔 𝟐 − 𝑪𝒂𝒓𝒃𝒐𝒏 𝟒 − 𝑪𝒂𝒓𝒃𝒐𝒏 𝟔 − 𝑪𝒂𝒓𝒃𝒐𝒏 𝟏𝟔 − 𝑪𝒂𝒓𝒃𝒐𝒏
  • 27. 𝐶16 ⋯ ⋯ − 𝐶 − 𝐶 − 𝐶 − 𝑺 − 𝑨𝑪𝑷 𝑂 𝐶16 ⋯ ⋯ − 𝐶 − 𝐶 − 𝐶 − 𝑂𝐻 𝑂 𝑇ℎ𝑖𝑜𝑒𝑠𝑡𝑒𝑟𝑎𝑠𝑒 𝐻2𝑂 ⟶ 𝑷𝒂𝒍𝒎𝒊𝒕𝒐𝒚𝒍 𝑨𝑪𝑷 𝑷𝒂𝒍𝒎𝒊𝒕𝒂𝒕𝒆 𝐴𝐶𝑃 − 𝑆𝐻
  • 28. • 1 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 + 7 [𝑀𝑎𝑙𝑜𝑛𝑦𝑙 𝐶𝑜𝐴] ⟶ 𝑃𝑎𝑙𝑚𝑖𝑡𝑎𝑡𝑒 • 7 × 2 𝑁𝐴𝐷𝑃𝐻 + 2𝐻+ ⟶ 7 × [2 𝑁𝐴𝐷𝑃+] • 8 𝐶𝑜𝐴𝑆𝐻 𝑎𝑟𝑒 𝑟𝑒𝑙𝑒𝑎𝑠𝑒𝑑. • 7 𝐶𝑂2 𝑎𝑟𝑒 𝑟𝑒𝑙𝑒𝑎𝑠𝑒𝑑 𝑑𝑢𝑒 𝑡𝑜 𝐶𝑜𝑛𝑑𝑒𝑛𝑠𝑎𝑡𝑖𝑜𝑛. • 7 𝐻2𝑂 𝑎𝑟𝑒 𝑟𝑒𝑙𝑒𝑎𝑠𝑒𝑑 𝑏𝑦 𝐷𝑒ℎ𝑦𝑑𝑟𝑎𝑡𝑖𝑜𝑛. • 1 𝐻2𝑂 𝑖𝑠 𝑢𝑠𝑒𝑑 𝑓𝑜𝑟 𝐻𝑦𝑑𝑟𝑜𝑙𝑦𝑠𝑖𝑠. 𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨 + 𝟕 𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑪𝒐𝑨 + 14 [𝑁𝐴𝐷𝑃𝐻 + 𝐻+] 𝑷𝒂𝒍𝒎𝒊𝒕𝒂𝒕𝒆 + 8 𝐶𝑜𝐴𝑆𝐻 + 7 𝐶𝑂2 + 6 𝐻2𝑂 + 14 𝑁𝐴𝐷𝑃+
  • 29. • 𝑁𝑜𝑤, 1 𝑀𝑎𝑙𝑜𝑛𝑦𝑙 𝐶𝑜𝐴 𝑖𝑠 𝑠𝑦𝑛𝑡ℎ𝑒𝑠𝑖𝑧𝑒𝑑 𝑓𝑟𝑜𝑚 1 𝐴𝑐𝑒𝑡𝑦𝑙 𝐶𝑜𝐴 𝑎𝑠 𝑓𝑜𝑙𝑙𝑜𝑤𝑠: 𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨 + 𝐴𝑇𝑃 𝑴𝒂𝒍𝒐𝒏𝒚𝒍 𝑪𝒐𝑨 + 𝐴𝐷𝑃 + 𝑃𝑖 +𝑯𝑪𝑶𝟑 − 𝟖 𝑨𝒄𝒆𝒕𝒚𝒍 𝑪𝒐𝑨 + 7 [𝐴𝑇𝑃 + 𝐻𝐶𝑂3 − ] + 14 [𝑁𝐴𝐷𝑃𝐻 + 𝐻+] 𝑷𝒂𝒍𝒎𝒊𝒕𝒂𝒕𝒆 + 8 𝐶𝑜𝐴𝑆𝐻 + 7 𝐶𝑂2 + 6 𝐻2𝑂 + 7 [𝐴𝐷𝑃 + 𝑃𝑖] + 14 𝑁𝐴𝐷𝑃+
  • 30. 𝐶𝐻2 − 𝑂𝐻 𝐶𝐻 − 𝑂𝐻 𝐶𝐻2 − 𝑂𝐻 𝐶𝐻2 − 𝑂𝐻 𝐶𝐻 − 𝑂𝐻 𝐶𝐻2 − 𝑂𝑃𝑂3 2− 𝐺𝑙𝑦𝑐𝑒𝑟𝑜𝑙 𝐾𝑖𝑛𝑎𝑠𝑒 𝑨𝑻𝑷 𝑨𝑫𝑷 𝑷𝒊 𝑮𝒍𝒚𝒄𝒆𝒓𝒐𝒍 𝟑 − 𝒑𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒆 𝑮𝒍𝒚𝒄𝒆𝒓𝒐𝒍 𝐶𝐻2 − 𝐶𝐻 − 𝑂𝐻 𝐶𝐻2 − 𝑂𝑃𝑂3 2− 𝐺𝑙𝑦𝑐𝑒𝑟𝑜𝑙 3 − 𝑃. 𝐴𝑐𝑦𝑙𝑡𝑟𝑎𝑛𝑠𝑓𝑒𝑟𝑎𝑠𝑒 𝑂 − 𝐶 − 𝑅1 𝑂 𝑭𝑨 − 𝑪𝒐𝑨 𝑪𝒐𝑨𝑺𝑯 𝑳𝒚𝒔𝒐𝒑𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒊𝒅𝒊𝒄 𝒂𝒄𝒊𝒅
  • 31. 𝐶𝐻2 − 𝐶𝐻 − 𝑂𝐻 𝐶𝐻2 − 𝑂𝑃𝑂3 2− 𝑂 − 𝐶 − 𝑅1 𝑂 𝑳𝒚𝒔𝒐𝒑𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒊𝒅𝒊𝒄 𝑨𝒄𝒊𝒅 𝐶𝐻2 − −𝐶𝐻 𝐶𝐻2 − 𝑂𝑃𝑂3 2− 𝑂 − 𝐶 − 𝑅1 𝑂 𝑷𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒊𝒅𝒊𝒄 𝑨𝒄𝒊𝒅 𝑅2 − 𝐶 − 𝑂 𝑂 𝐴𝑐𝑦𝑙𝑔𝑙𝑦𝑐𝑒𝑟𝑜𝑝ℎ𝑜𝑠𝑝ℎ𝑎𝑡𝑒 𝐴𝑐𝑦𝑙𝑡𝑟𝑎𝑛𝑠𝑓𝑒𝑟𝑎𝑠𝑒
  • 32. 𝐶𝐻2 − −𝐶𝐻 𝐶𝐻2 − 𝑂𝐻 𝑂 − 𝐶 − 𝑅1 𝑂 𝑷𝒉𝒐𝒔𝒑𝒉𝒂𝒕𝒊𝒅𝒊𝒄 𝑨𝒄𝒊𝒅 𝑅2 − 𝐶 − 𝑂 𝑂 𝑫𝒊𝒂𝒄𝒚𝒍𝒈𝒍𝒚𝒄𝒆𝒓𝒐𝒍 𝑻𝒓𝒊𝒂𝒄𝒚𝒍𝒈𝒍𝒚𝒄𝒆𝒓𝒐𝒍 𝐶𝐻2 − −𝐶𝐻 𝐶𝐻2 − 𝑂 − 𝐶 − 𝑅1 𝑂 𝑅2 − 𝐶 − 𝑂 𝑂 𝑂 − 𝐶 − 𝑅3 𝑂 𝐷𝑖𝑎𝑐𝑦𝑙𝑔𝑙𝑦𝑐𝑒𝑟𝑜𝑙 𝐴𝑐𝑦𝑙𝑡𝑟𝑎𝑛𝑠𝑓𝑒𝑟𝑎𝑠𝑒 𝑭𝑨 − 𝑪𝒐𝑨 ⟶