Feng Cheng1,2, Shu-Ping Zou1,2, Jian-Miao Xu1,2, Heng Tang1,2, Ya-Ping Xue1,2, Yu-Guo Zheng1,2
Published:
2024-07-02
Contact:
Ya-Ping Xue
程峰1,2, 邹树平1,2, 徐建妙1,2, 汤恒1,2, 薛亚平1,2, 郑裕国1,2
通讯作者:
薛亚平
作者简介:
Feng Cheng, Shu-Ping Zou, Jian-Miao Xu, Heng Tang, Ya-Ping Xue, Yu-Guo Zheng. BioHiPP TM: A Benchmark of Biomanufacturing for High Optically PureL-Phosphinothricin[J]. Synthetic Biology Journal, DOI: 10.12211/2096-8280.2024-032.
程峰, 邹树平, 徐建妙, 汤恒, 薛亚平, 郑裕国. 生物高纯精草:高光学纯L-草铵膦生物制造的创新与发展[J]. 合成生物学, DOI: 10.12211/2096-8280.2024-032.
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URL: https://synbioj.cip.com.cn/EN/10.12211/2096-8280.2024-032
Fig.1 Three industrial production routes of D,L-PPT. (A) Thermal cracking-ACA process (referred to as "Gas phase synthesis"); (B) Grignard-strecker process (referred to as "Grignard synthesis"); (C) Aluminum-strecker process (referred to as "Aluminum synthesis")
工艺 条目 | 热裂解-ACA工艺 (“气相合成”) | 铝法-Strecker工艺 (“铝法合成”) | 格氏-Strecker工艺 (“格氏合成”) |
---|---|---|---|
连续化程度 | 完全连续化 | 半连续化 | 间歇化 |
工艺特点 | 连续化程度高 对反应器装置要求高 | 工艺简单, 易燃易爆,使用剧毒氰化物,分离纯化困难 | 工艺简单, 易燃易爆,使用剧毒氰化物,分离纯化困难 |
三废排放 | 固废量少,可用来制备高附加值产品 | 固废量大 | 废水量大 |
生产成本 | 5-6万元/吨 | 6-7万元/吨 | 7-8万元/吨 |
Table 1 Comparison of three production processes for D,L-PPT
工艺 条目 | 热裂解-ACA工艺 (“气相合成”) | 铝法-Strecker工艺 (“铝法合成”) | 格氏-Strecker工艺 (“格氏合成”) |
---|---|---|---|
连续化程度 | 完全连续化 | 半连续化 | 间歇化 |
工艺特点 | 连续化程度高 对反应器装置要求高 | 工艺简单, 易燃易爆,使用剧毒氰化物,分离纯化困难 | 工艺简单, 易燃易爆,使用剧毒氰化物,分离纯化困难 |
三废排放 | 固废量少,可用来制备高附加值产品 | 固废量大 | 废水量大 |
生产成本 | 5-6万元/吨 | 6-7万元/吨 | 7-8万元/吨 |
Fig.2 Schematic diagram of racemate derivatization-resolution route. (A) Acetylation of racemic PPT, followed by dynamic splitting synthesis using acetyl-PPT as substrate to obtain L-PPT; (B) Benzoylation of racemic PPT, followed by dynamic splitting synthesis using benzoyl-PPT as substrate to obtain L-PPT
通用化合物氰基化再水解路线 | 外消旋D,L-草铵膦为底物的 混旋体合成-去消旋化路线 | 从常用化学品合成L-草铵膦路线 | 从头合成高丝氨酸再化学合成路线 | ||||
---|---|---|---|---|---|---|---|
生物拆分 | 生物有机胺胺化 | 生物无机氨胺化 | 生物无机胺胺化 | 生物有机胺胺化 | |||
生物 催化剂 | 腈水解酶等 | 酰化酶、酰胺酶等 | 氧化酶/多个转氨酶 | D-氧化酶/ L-脱氢酶等 | 脱氢酶等 | 转氨酶 | 生物发酵 |
供体 | 无 | 无 | 3-4倍当量有机胺 | 无机氨 | 无机氨 | 2-4倍当量有机胺 | 无机膦/有机膦 |
底物 | 氨基腈 | 草铵膦衍生物 | D,L-草铵膦 | D,L-草铵膦 | 潜手性酮 | D,L-草铵膦 | 葡糖糖 |
转化率/ 产物e.e.值 | 86%/ >99% | <50%/ >99% | 90-99%/ >99% | 100%/ >99% | <100%/ >99% | 90-99%/ >99% | e.e.>99% |
分离 纯化 | 容易 | 容易 | 困难 | 容易 | 容易 | 困难 | 容易 |
(原粉、水剂) | (原粉、水剂) | (水剂) | (原粉、水剂) | (原粉、水剂) | (水剂) | (原粉、水剂) |
Table 2 Comparison of four technical routes for L-PPT
通用化合物氰基化再水解路线 | 外消旋D,L-草铵膦为底物的 混旋体合成-去消旋化路线 | 从常用化学品合成L-草铵膦路线 | 从头合成高丝氨酸再化学合成路线 | ||||
---|---|---|---|---|---|---|---|
生物拆分 | 生物有机胺胺化 | 生物无机氨胺化 | 生物无机胺胺化 | 生物有机胺胺化 | |||
生物 催化剂 | 腈水解酶等 | 酰化酶、酰胺酶等 | 氧化酶/多个转氨酶 | D-氧化酶/ L-脱氢酶等 | 脱氢酶等 | 转氨酶 | 生物发酵 |
供体 | 无 | 无 | 3-4倍当量有机胺 | 无机氨 | 无机氨 | 2-4倍当量有机胺 | 无机膦/有机膦 |
底物 | 氨基腈 | 草铵膦衍生物 | D,L-草铵膦 | D,L-草铵膦 | 潜手性酮 | D,L-草铵膦 | 葡糖糖 |
转化率/ 产物e.e.值 | 86%/ >99% | <50%/ >99% | 90-99%/ >99% | 100%/ >99% | <100%/ >99% | 90-99%/ >99% | e.e.>99% |
分离 纯化 | 容易 | 容易 | 困难 | 容易 | 容易 | 困难 | 容易 |
(原粉、水剂) | (原粉、水剂) | (水剂) | (原粉、水剂) | (原粉、水剂) | (水剂) | (原粉、水剂) |
酶类 | 国际酶学 编号 | 辅酶再生 底物 | 辅酶再 生产物 | 优点 | 缺点 |
---|---|---|---|---|---|
FDH | EC 1.2.1.2 | 甲酸(铵) | CO2和水 | 副产物CO2无毒具挥发性易于分离 | 催化效率低,底物亲和力差,具NAD+特异性 |
GDH | EC 1.1.1.47 | 葡萄糖 | 葡萄糖酸 | 催化活力高,辅底物价格低廉 | 副产物易溶于水难以分离,反应pH降低需要调控 |
ADH | EC 1.1.1.1-2 | 异丙醇 | 丙酮 | 催化活力较高,副产物沸点低易除去 | 反应可逆,副产物可能会影响酶活 |
Table 3 Classification and characteristics of coenzyme regeneration enzymes
酶类 | 国际酶学 编号 | 辅酶再生 底物 | 辅酶再 生产物 | 优点 | 缺点 |
---|---|---|---|---|---|
FDH | EC 1.2.1.2 | 甲酸(铵) | CO2和水 | 副产物CO2无毒具挥发性易于分离 | 催化效率低,底物亲和力差,具NAD+特异性 |
GDH | EC 1.1.1.47 | 葡萄糖 | 葡萄糖酸 | 催化活力高,辅底物价格低廉 | 副产物易溶于水难以分离,反应pH降低需要调控 |
ADH | EC 1.1.1.1-2 | 异丙醇 | 丙酮 | 催化活力较高,副产物沸点低易除去 | 反应可逆,副产物可能会影响酶活 |
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