HATU

HATU
	首选IUPAC名; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
识别
CAS号	148893-10-1
PubChem	9886157
ChemSpider	8061830
SMILES	CN(C)C(=[N+](C)C)On1c2c(cccn2)nn1.F[P-](F)(F)(F)(F)F;
InChI	1/C10H15N6O.F6P/c1-14(2)10(15(3)4)17-16-9-8(12-13-16)6-5-7-11-9;1-7(2,3,4,5)6/h5-7H,1-4H3;/q+1;-1;
InChIKey	JNWBBCNCSMBKNE-UHFFFAOYAG
性质
化学式	C10H15F6N6OP
摩尔质量	380.23 g·mol−1
外观	白色晶体粉末
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

HATU（缩写自Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium，六氟磷酸氮杂苯并三唑四甲基脲^[1]）是一种多肽偶联的试剂，可将羧酸转化为活性酯。它通常在二甲基甲酰胺或其它极性非质子溶剂中与二异丙基乙胺、三乙胺一起使用以构筑酰胺键。^[2]

HATU的反应机理如下：^[3]

安全

HATU有潜在的致敏性。^[4]差示扫描量热测试（DSC）表明，它具有爆炸风险。^[5]

参考文献

^ 注释：HATU可以以脲盐（O-异构体）或活性较弱的亚铵盐（N-异构体）形式存在。
^ Amine to Amide (Coupling) - HATU. [2026-01-17]. （原始内容存档于2024-09-08）.
^ Carpino, Louis A; Imazumi, Hideko; Foxman, Bruce M; Vela, Michael J; Henklein, Peter; El-Faham, Ayman; Klose, Jana; Bienert, Michael. Comparison of the Effects of 5- and 6-HOat on Model Peptide Coupling Reactions Relative to the Cases for the 4- and 7-Isomers†,‡. Organic Letters. 2000, 2 (15): 2253–2256. PMID 10930256. doi:10.1021/ol006013z.
^ McKnelly, Kate J.; Sokol, William; Nowick, James S. Anaphylaxis Induced by Peptide Coupling Agents: Lessons Learned from Repeated Exposure to HATU, HBTU, and HCTU. The Journal of Organic Chemistry. 2020-02-07, 85 (3): 1764–1768 [2026-01-16]. ISSN 0022-3263. PMID 31849224. doi:10.1021/acs.joc.9b03280. （原始内容存档于2025-08-02）（英语）.
^ Sperry, Jeffrey B.; Minteer, Christopher J.; Tao, JingYa; Johnson, Rebecca; Duzguner, Remzi; Hawksworth, Michael; Oke, Samantha; Richardson, Paul F.; Barnhart, Richard; Bill, David R.; Giusto, Robert A.; Weaver, John D. Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing. Organic Process Research & Development. 2018-09-21, 22 (9): 1262–1275 [2026-01-16]. ISSN 1083-6160. doi:10.1021/acs.oprd.8b00193. （原始内容存档于2024-12-04）（英语）.

[1] 注释：HATU可以以脲盐（O-异构体）或活性较弱的亚铵盐（N-异构体）形式存在。

[2] Amine to Amide (Coupling) - HATU. [2026-01-17]. （原始内容存档于2024-09-08）.

[3] Carpino, Louis A; Imazumi, Hideko; Foxman, Bruce M; Vela, Michael J; Henklein, Peter; El-Faham, Ayman; Klose, Jana; Bienert, Michael. Comparison of the Effects of 5- and 6-HOat on Model Peptide Coupling Reactions Relative to the Cases for the 4- and 7-Isomers†,‡. Organic Letters. 2000, 2 (15): 2253–2256. PMID 10930256. doi:10.1021/ol006013z.

[4] McKnelly, Kate J.; Sokol, William; Nowick, James S. Anaphylaxis Induced by Peptide Coupling Agents: Lessons Learned from Repeated Exposure to HATU, HBTU, and HCTU. The Journal of Organic Chemistry. 2020-02-07, 85 (3): 1764–1768 [2026-01-16]. ISSN 0022-3263. PMID 31849224. doi:10.1021/acs.joc.9b03280. （原始内容存档于2025-08-02）（英语）.

[5] Sperry, Jeffrey B.; Minteer, Christopher J.; Tao, JingYa; Johnson, Rebecca; Duzguner, Remzi; Hawksworth, Michael; Oke, Samantha; Richardson, Paul F.; Barnhart, Richard; Bill, David R.; Giusto, Robert A.; Weaver, John D. Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing. Organic Process Research & Development. 2018-09-21, 22 (9): 1262–1275 [2026-01-16]. ISSN 1083-6160. doi:10.1021/acs.oprd.8b00193. （原始内容存档于2024-12-04）（英语）.

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