Zijian LIU1,2, Baiyang MU3, Zhiqiang DUAN1, Xuan WANG1, Xiaojie LU1,2
Received:
2024-01-17
Revised:
2024-05-30
Published:
2024-06-11
Contact:
Xiaojie LU
刘子健1,2, 穆柏杨3, 段志强1, 王璇1, 陆晓杰1,2
通讯作者:
陆晓杰
作者简介:
基金资助:
CLC Number:
Zijian LIU, Baiyang MU, Zhiqiang DUAN, Xuan WANG, Xiaojie LU. Advances in the development of DNA-compatible chemistries[J]. Synthetic Biology Journal, DOI: 10.12211/2096-8280.2024-008.
刘子健, 穆柏杨, 段志强, 王璇, 陆晓杰. 与核酸兼容的化学反应开发进展[J]. 合成生物学, DOI: 10.12211/2096-8280.2024-008.
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URL: https://synbioj.cip.com.cn/EN/10.12211/2096-8280.2024-008
条目 | 反应式 | 反应条件 | 参考文献 |
---|---|---|---|
1 | ![]() | Pd (PPh3)4, Na2CO3, H2O/DMA/CH3CN, 80 ℃. | [ |
2 | ![]() | POPd/sSPhos, KOH, H2O/DMA, 80 ℃. | [ |
3 | ![]() | Pd(OAc)2, Et3N H2O/DMA, rt, 2h. | [ |
4 | ![]() | Pd(OAc)2, Et3N H2O/DMA, rt, 2h. | [ |
5 | ![]() | Pd(OAc)2, (rac)-BIDIME, K2CO3, DMA/H2O, 95℃, 2 h. | [ |
6 | ![]() | Pd(OAc)2/TPPTS, K2CO3, H2O/DMA, 70℃, 2 h | [ |
7 | ![]() | Na2PdCl4/sSPhos, K2CO3, H2O/ACN, 37℃, 28 h | [ |
8 | ![]() | [Ru], KOAc, DMF/H2O, 60℃, 10 h. | [ |
9 | ![]() | 1: PdCl2(dppf)DCM, K2CO3, DMSO/H2O, 80 ℃ 2: PdCl2(COD), NaOAc, DMA/H2O, 80 ℃ | [ |
Table 1 Metal-catalyzed C(sp2)-C(sp2) bond formation reactions
条目 | 反应式 | 反应条件 | 参考文献 |
---|---|---|---|
1 | ![]() | Pd (PPh3)4, Na2CO3, H2O/DMA/CH3CN, 80 ℃. | [ |
2 | ![]() | POPd/sSPhos, KOH, H2O/DMA, 80 ℃. | [ |
3 | ![]() | Pd(OAc)2, Et3N H2O/DMA, rt, 2h. | [ |
4 | ![]() | Pd(OAc)2, Et3N H2O/DMA, rt, 2h. | [ |
5 | ![]() | Pd(OAc)2, (rac)-BIDIME, K2CO3, DMA/H2O, 95℃, 2 h. | [ |
6 | ![]() | Pd(OAc)2/TPPTS, K2CO3, H2O/DMA, 70℃, 2 h | [ |
7 | ![]() | Na2PdCl4/sSPhos, K2CO3, H2O/ACN, 37℃, 28 h | [ |
8 | ![]() | [Ru], KOAc, DMF/H2O, 60℃, 10 h. | [ |
9 | ![]() | 1: PdCl2(dppf)DCM, K2CO3, DMSO/H2O, 80 ℃ 2: PdCl2(COD), NaOAc, DMA/H2O, 80 ℃ | [ |
条目 | DNA兼容反应 | 反应条件 | 参考文献 |
---|---|---|---|
1 | ![]() | CuOTf, TBHP ACN/H2O, 50/70 ℃, 10 h | [ |
2 | ![]() | a: Pd(OAc)2, AgOAc, Li2CO3, H2O/DMA, 80℃, 20 h. b: Pd(OAc)2/ligand AgTFA, NaOAc H2O/DMA, 80℃, 20 h. | [ |
Table 2 Metal-catalyzed C(sp2)-C(sp3) and C(sp2)-C(sp) bond formation reactions
条目 | DNA兼容反应 | 反应条件 | 参考文献 |
---|---|---|---|
1 | ![]() | CuOTf, TBHP ACN/H2O, 50/70 ℃, 10 h | [ |
2 | ![]() | a: Pd(OAc)2, AgOAc, Li2CO3, H2O/DMA, 80℃, 20 h. b: Pd(OAc)2/ligand AgTFA, NaOAc H2O/DMA, 80℃, 20 h. | [ |
条目 | DNA兼容反应 | 反应条件 | 参考文献 |
---|---|---|---|
1 | ![]() | t-BuXPhos Pd G1, CsOH, H2O/DMA, 100 ℃, 3 h. | [ |
2 | ![]() | t-Brettphos Pd G3, Et3N, H2O/DMA, 60 ℃, 2h. | [ |
3 | ![]() | t-BuXPhos-Pd-G3, NaOH, H2O/DMA, 60 ℃, 2 h. | [ |
4 | ![]() | Pd-PEPPSI-iPentCl-pyr, Na ascorbate, CsOH, DMA/H2O, 95 ℃, 15min | [ |
5 | ![]() | Pd(OAc)2/BippyPhos, Na ascorbate, K3PO4, DMA/H2O, 95 ℃, 15min. | [ |
6 | ![]() | t-BuXPhos-Pd-G1, NaOH, H2O/DMA, 80 ℃, 3 h. | [ |
7 | ![]() | 1: CuSO4·5H2O, Na ascorbate, H2O/DMA, 100 ℃, 2 h. 2: CuSO4·5H2O, Proline, KOH, Na ascorbate, H2O/DMA, 100 ℃, 2 h. | [ |
8 | ![]() | Cu(OAc)2 /ligand, Na ascorbate, K3PO4, DMSO/H2O, 40℃, 3 h. | [ |
9 | ![]() | a: K2CO3 or KOH, DMA/H2O, rt, or 60 ℃, 10 h b: K2CO3, DMA/H2O, rt, or 80 ℃, 10 h | [ |
10 | ![]() | [Rh], PBS (pH 4.2)-DMA (7:1) 80 ℃, 6h | [ |
11 | ![]() | a: I2, BSA, MeOH/H2O, 40, ℃, 150 min b: (1) BME, RT, 10 min (2) I2, BSA, MeOH/H2O, 40, ℃, 150 min | [ |
Table 3 Metal-catalyzed C-X coupling reactions
条目 | DNA兼容反应 | 反应条件 | 参考文献 |
---|---|---|---|
1 | ![]() | t-BuXPhos Pd G1, CsOH, H2O/DMA, 100 ℃, 3 h. | [ |
2 | ![]() | t-Brettphos Pd G3, Et3N, H2O/DMA, 60 ℃, 2h. | [ |
3 | ![]() | t-BuXPhos-Pd-G3, NaOH, H2O/DMA, 60 ℃, 2 h. | [ |
4 | ![]() | Pd-PEPPSI-iPentCl-pyr, Na ascorbate, CsOH, DMA/H2O, 95 ℃, 15min | [ |
5 | ![]() | Pd(OAc)2/BippyPhos, Na ascorbate, K3PO4, DMA/H2O, 95 ℃, 15min. | [ |
6 | ![]() | t-BuXPhos-Pd-G1, NaOH, H2O/DMA, 80 ℃, 3 h. | [ |
7 | ![]() | 1: CuSO4·5H2O, Na ascorbate, H2O/DMA, 100 ℃, 2 h. 2: CuSO4·5H2O, Proline, KOH, Na ascorbate, H2O/DMA, 100 ℃, 2 h. | [ |
8 | ![]() | Cu(OAc)2 /ligand, Na ascorbate, K3PO4, DMSO/H2O, 40℃, 3 h. | [ |
9 | ![]() | a: K2CO3 or KOH, DMA/H2O, rt, or 60 ℃, 10 h b: K2CO3, DMA/H2O, rt, or 80 ℃, 10 h | [ |
10 | ![]() | [Rh], PBS (pH 4.2)-DMA (7:1) 80 ℃, 6h | [ |
11 | ![]() | a: I2, BSA, MeOH/H2O, 40, ℃, 150 min b: (1) BME, RT, 10 min (2) I2, BSA, MeOH/H2O, 40, ℃, 150 min | [ |
条目 | DNA兼容反应 | 反应条件 | 参考文献 |
---|---|---|---|
1 | ![]() | [Ir], blue light, K2HPO4, DMSO/H2O, N2, rt, 6 h. | [ |
2 | ![]() | [Ir], blue light, DMSO/H2O, glycerol, rt, 2 h. | [ |
3 | ![]() | [Ir], blue light, K2HPO4, DMSO/H2O, N2, rt, 2 h. | [ |
4 | ![]() | [Ir], blue light, quinuclidine, DMSO/H2O, N2, rt, 45 min. | [ |
5 | ![]() | [Ru], blue light, Hantzsch ester, 4-methylbenzenethiol DMA/H2O, rt, 3 h. | [ |
6 | ![]() | [Ru], blue light, I2, DMA/H2O, rt, 3 h. | |
7 | ![]() | [Ir], blue light, quinuclidine, DMF/H2O, N2, rt, 1.5 h. | [ |
8 | ![]() | [Ir], blue light, 2,6-lutidine, DMSO/H2O, rt, 10 min. | [ |
9 | ![]() | [Ir], kessil lamp, DMSO/H2O, rt, 5 min. | [ |
10 | ![]() | Hantzsch ester, blue Kessil, DMSO/H2O, rt, 5 min. | [ |
Table 4 Photocatalytic C(sp3)-C(sp3) bond formation reactions
条目 | DNA兼容反应 | 反应条件 | 参考文献 |
---|---|---|---|
1 | ![]() | [Ir], blue light, K2HPO4, DMSO/H2O, N2, rt, 6 h. | [ |
2 | ![]() | [Ir], blue light, DMSO/H2O, glycerol, rt, 2 h. | [ |
3 | ![]() | [Ir], blue light, K2HPO4, DMSO/H2O, N2, rt, 2 h. | [ |
4 | ![]() | [Ir], blue light, quinuclidine, DMSO/H2O, N2, rt, 45 min. | [ |
5 | ![]() | [Ru], blue light, Hantzsch ester, 4-methylbenzenethiol DMA/H2O, rt, 3 h. | [ |
6 | ![]() | [Ru], blue light, I2, DMA/H2O, rt, 3 h. | |
7 | ![]() | [Ir], blue light, quinuclidine, DMF/H2O, N2, rt, 1.5 h. | [ |
8 | ![]() | [Ir], blue light, 2,6-lutidine, DMSO/H2O, rt, 10 min. | [ |
9 | ![]() | [Ir], kessil lamp, DMSO/H2O, rt, 5 min. | [ |
10 | ![]() | Hantzsch ester, blue Kessil, DMSO/H2O, rt, 5 min. | [ |
条目 | DNA兼容反应 | 反应条件 | 参考文献 |
---|---|---|---|
1 | ![]() | a: 4CzIPN, Ni(TMHD)2, blue LED, DMSO/H2O, 45 min, b: [Ir], Ni(TMHD)2, blue LED, TMG, MOPS pH 8 buffer, DMSO/H2O, 10 min, | [ |
2 | ![]() | [Ir], [Ni], blue kessil, MgCl2, Et3N, DMSO/H2O, rt, 45 min. | [ |
3 | ![]() | [Ir], [Ni], blue kessil, DMSO/H2O, rt, 15 min. | |
4 | ![]() | [Ir], Hantzsch ester, blue kessil, DMSO/H2O, rt, 5 min. | [ |
5 | ![]() | [Ir], DIPEA, blue Kessil, DMSO/H2O, rt, 5 min. | [ |
Table 5 Photocatalytic C(sp2)-C bond formation reactions
条目 | DNA兼容反应 | 反应条件 | 参考文献 |
---|---|---|---|
1 | ![]() | a: 4CzIPN, Ni(TMHD)2, blue LED, DMSO/H2O, 45 min, b: [Ir], Ni(TMHD)2, blue LED, TMG, MOPS pH 8 buffer, DMSO/H2O, 10 min, | [ |
2 | ![]() | [Ir], [Ni], blue kessil, MgCl2, Et3N, DMSO/H2O, rt, 45 min. | [ |
3 | ![]() | [Ir], [Ni], blue kessil, DMSO/H2O, rt, 15 min. | |
4 | ![]() | [Ir], Hantzsch ester, blue kessil, DMSO/H2O, rt, 5 min. | [ |
5 | ![]() | [Ir], DIPEA, blue Kessil, DMSO/H2O, rt, 5 min. | [ |
条目 | 杂环结构 | 合成策略 | 参考文献 |
---|---|---|---|
1 | ![]() | 醛和α-氯代酮缩合环化 | [ |
2 | ![]() | 醛、氨基酸和异腈之间多组分缩合环化 | [ |
3 | ![]() | Clauson-Kaas反应合成吡咯核心; 再通过碘代和交叉偶联实现功能化 | [ |
4 | ![]() | 醛、苯磺酰肼和重氮盐环化生成二取代四唑;再与末端烯烃进行环加成反应 | [ |
5 | ![]() | 环氧化物开环生成β-氨基醇, 再与氯甲酸酯环化 | [ |
6 | ![]() | 羟胺和腈生成偕胺肟, 再由羧酸酰化后发生脱水环化 | [ |
7 | ![]() | 苯甲酰肼与醛缩合环化 | [ |
8 | ![]() | 芳基硼酸先转化芳基叠氮化物, 再与炔进行环加成 | [ |
9 | ![]() | 腈与叠氮化物之间的环加成反应 | [ |
10 | ![]() | 环氧化物开环生成β-氨基醇, 再与氯乙酰氯环化 | [ |
11 | ![]() | 四嗪与烯基/羰基化合物进行IEDDA反应(烯基产物需要额外氧化) | [ |
12 | ![]() | 烯醇前体与羰基化合物和丙二腈之间的多组分缩合环化反应 | [ |
Table 6 Single-ring synthesis reactions
条目 | 杂环结构 | 合成策略 | 参考文献 |
---|---|---|---|
1 | ![]() | 醛和α-氯代酮缩合环化 | [ |
2 | ![]() | 醛、氨基酸和异腈之间多组分缩合环化 | [ |
3 | ![]() | Clauson-Kaas反应合成吡咯核心; 再通过碘代和交叉偶联实现功能化 | [ |
4 | ![]() | 醛、苯磺酰肼和重氮盐环化生成二取代四唑;再与末端烯烃进行环加成反应 | [ |
5 | ![]() | 环氧化物开环生成β-氨基醇, 再与氯甲酸酯环化 | [ |
6 | ![]() | 羟胺和腈生成偕胺肟, 再由羧酸酰化后发生脱水环化 | [ |
7 | ![]() | 苯甲酰肼与醛缩合环化 | [ |
8 | ![]() | 芳基硼酸先转化芳基叠氮化物, 再与炔进行环加成 | [ |
9 | ![]() | 腈与叠氮化物之间的环加成反应 | [ |
10 | ![]() | 环氧化物开环生成β-氨基醇, 再与氯乙酰氯环化 | [ |
11 | ![]() | 四嗪与烯基/羰基化合物进行IEDDA反应(烯基产物需要额外氧化) | [ |
12 | ![]() | 烯醇前体与羰基化合物和丙二腈之间的多组分缩合环化反应 | [ |
条目 | 杂环结构 | 合成策略 | 参考文献 |
---|---|---|---|
1 | ![]() | 伯胺与邻苯二甲醛缩合环化反应 | [ |
2 | ![]() | 伯胺、邻苯二甲醛和4-叔丁基苯硫醇之间的 多组分缩合环化反应 | |
3 | ![]() | 苯胺与醛缩合生成的亚胺, 由布朗斯特酸活化后进行烯烃亲电加成、 苯环亲电取代环化和消除反应 | [ |
4 | ![]() | 苯乙炔和1,6-庚二炔之间的环加成反应 | [ |
5 | ![]() | 靛红与醛在苯甲酰肼促进下的环加成反应 | [ |
6 | ![]() | 芳基伯胺与TCDI反应生成异硫氰酸酯, 再与邻位仲胺生成硫脲;最后脱硫环化 | [ |
7 | ![]() | 硝基芳烃经硼酸还原为亚硝基中间体, 再与邻位酰胺氮原子亲核加成 | [ |
8 | ![]() | 醛与邻氨基苯甲酰胺或醛与靛红酸酐和伯胺 进行环化反应,再对环化产物进行氧化 | [ |
9 | ![]() | 苯甲酸C-H活化后与炔发生环加成反应 | [ |
10 | ![]() | 醛、邻苯二胺和1,3-二羰基化合物之间的 多组分缩合环化反应 | [ |
Table 7 Fused-ring synthesis reactions
条目 | 杂环结构 | 合成策略 | 参考文献 |
---|---|---|---|
1 | ![]() | 伯胺与邻苯二甲醛缩合环化反应 | [ |
2 | ![]() | 伯胺、邻苯二甲醛和4-叔丁基苯硫醇之间的 多组分缩合环化反应 | |
3 | ![]() | 苯胺与醛缩合生成的亚胺, 由布朗斯特酸活化后进行烯烃亲电加成、 苯环亲电取代环化和消除反应 | [ |
4 | ![]() | 苯乙炔和1,6-庚二炔之间的环加成反应 | [ |
5 | ![]() | 靛红与醛在苯甲酰肼促进下的环加成反应 | [ |
6 | ![]() | 芳基伯胺与TCDI反应生成异硫氰酸酯, 再与邻位仲胺生成硫脲;最后脱硫环化 | [ |
7 | ![]() | 硝基芳烃经硼酸还原为亚硝基中间体, 再与邻位酰胺氮原子亲核加成 | [ |
8 | ![]() | 醛与邻氨基苯甲酰胺或醛与靛红酸酐和伯胺 进行环化反应,再对环化产物进行氧化 | [ |
9 | ![]() | 苯甲酸C-H活化后与炔发生环加成反应 | [ |
10 | ![]() | 醛、邻苯二胺和1,3-二羰基化合物之间的 多组分缩合环化反应 | [ |
条目 | 杂环结构 | 合成策略 | 参考文献 |
---|---|---|---|
1 | ![]() | 丙烯酰胺、靛红和脯氨酸之间的三组份环化反应 | [ |
2 | ![]() | 3-重氮吲哚酮和缺电子烯烃之间的环加成反应 | |
3 | ![]() | 靛红、烯醇化物和丙二腈之间的环化反应 | [ |
4 | ![]() | 靛红和邻氨基苯甲酰胺之间的缩合环化反应 | [ |
5 | ![]() | 亚甲基环丁烷与不饱和杂环分子间的 光环加成反应 | [ |
Table 8 Spiro-ring synthesis reactions
条目 | 杂环结构 | 合成策略 | 参考文献 |
---|---|---|---|
1 | ![]() | 丙烯酰胺、靛红和脯氨酸之间的三组份环化反应 | [ |
2 | ![]() | 3-重氮吲哚酮和缺电子烯烃之间的环加成反应 | |
3 | ![]() | 靛红、烯醇化物和丙二腈之间的环化反应 | [ |
4 | ![]() | 靛红和邻氨基苯甲酰胺之间的缩合环化反应 | [ |
5 | ![]() | 亚甲基环丁烷与不饱和杂环分子间的 光环加成反应 | [ |
条目 | 多功能核心 | 衍生杂环 | 参考文献 |
---|---|---|---|
1 | ![]() | ![]() | [ |
2 | ![]() | ![]() | [ |
3 | ![]() | ![]() | [ |
4 | ![]() | ![]() | [ |
Table 9 DOS-directed Privileged heterocycles synthesis reactions
条目 | 多功能核心 | 衍生杂环 | 参考文献 |
---|---|---|---|
1 | ![]() | ![]() | [ |
2 | ![]() | ![]() | [ |
3 | ![]() | ![]() | [ |
4 | ![]() | ![]() | [ |
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