Direct Conversion of Hydrazones to Amines using Transaminases.
Direct Conversion of Hydrazones to Amines using Transaminases.
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DOI：
10.1002/cctc.202101008
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发表时间：
2021-11-08
期刊：
影响因子：
4.5
通讯作者：
Hailes, Helen C.
中科院分区：
文献类型：
--
作者：
Carter, Eve M.;Subrizi, Fabiana;Ward, John M.;Sheppard, Tom D.;Hailes, Helen C.
氨基转移酶（TAm）已被广泛用于醛和酮的胺化，通常产生光学纯的产物。在这项工作中，转氨酶直接与腙反应，在一个新的方法，形成胺产品。研究了几种底物，包括具有呋喃和苯基部分的底物。经测定，当向反应混合物中加入另外的亲电试剂时，胺产率增加，表明它们可以螯合反应中释放的肼。发现5 '-磷酸吡哆醛（PLP）（转氨酶的辅因子）和聚乙二醇（PEG）-醛都能增加形成的胺的产率。值得注意的是，（S）-（-）-1-氨基-2-（甲氧基甲基）吡咯烷（SAMP）腙的胺化作为以良好产率形成手性β-取代胺的方法给出了有希望的结果。醛和酮与转氨酶的反应已广泛用于生产胺。在这里，一个新的腙和转氨酶之间的转换进行了探索。研究了几种底物，以良好的产率形成各种胺。胺产率被发现通过添加亲电试剂来提高，亲电试剂被认为是“捕获”反应中释放的肼。
Transaminase enzymes (TAms) have been widely used for the amination of aldehydes and ketones, often resulting in optically pure products. In this work, transaminases were directly reacted with hydrazones in a novel approach to form amine products. Several substrates were investigated, including those with furan and phenyl moieties. It was determined that the amine yields increased when an additional electrophile was added to the reaction mixture, suggesting that they can sequester the hydrazine released in the reaction. Pyridoxal 5’‐phosphate (PLP), a cofactor for transaminases, and polyethylene glycol (PEG)‐aldehydes were both found to increase the yield of amine formed. Notably, the amination of (S)‐(−)‐1‐amino‐2‐(methoxymethyl)pyrrolidine (SAMP) hydrazones gave promising results as a method to form chiral β‐substituted amines in good yield. The reaction of aldehydes and ketones with transaminases has been widely used for producing amines. Here, a new transformation between hydrazones and transaminases was explored. Several substrates were investigated, forming a variety of amines in good yields. Amine yields were found to improve by the addition of electrophiles, thought to ‘trap’ the hydrazine released in the reaction.
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影响因子：
9.8
作者：
Higson, Sally;Subrizi, Fabiana;Hailes, Helen C.
通讯作者：
Hailes, Helen C.
影响因子：
3.4
作者：
Kroutil W;Fischereder EM;Fuchs CS;Lechner H;Mutti FG;Pressnitz D;Rajagopalan A;Sattler JH;Simon RC;Siirola E
通讯作者：
Siirola E
影响因子：
56.9
作者：
Savile, Christopher K.;Janey, Jacob M.;Hughes, Gregory J.
通讯作者：
Hughes, Gregory J.
影响因子：
12.9
作者：
Velikogne S;Breukelaar WB;Hamm F;Glabonjat RA;Kroutil W
通讯作者：
Kroutil W
DOI：
10.1002/chem.201503510
发表时间：
2015-11-02
期刊：
Chemistry (Weinheim an der Bergstrasse, Germany)
影响因子：
--
作者：
Foster RW;Tame CJ;Bučar DK;Hailes HC;Sheppard TD
通讯作者：
Sheppard TD