Direct Conversion of Hydrazones to Amines using Transaminases

被引：5

作者：

Carter, Eve M. ^{[1
]}

Subrizi, Fabiana ^{[1
]}

Ward, John M. ^{[2
]}

Sheppard, Tom D. ^{[1
]}

Hailes, Helen C. ^{[1
]}

机构：

[1] UCL, Dept Chem, 20 Gordon St, London WC1H 0AJ, England

[2] UCL, Dept Biochem Engn, Gower St,Bernard Katz Bldg, London WC1E 6BT, England

来源：

CHEMCATCHEM | 2021年 / 13卷 / 21期

基金：

英国工程与自然科学研究理事会; 英国生物技术与生命科学研究理事会;

关键词：

amines; biocatalysis; enzymes; hydrazones; transaminases; ENANTIOSELECTIVE SYNTHESIS; BIOCATALYTIC STRATEGIES; ALPHA-ALKYLATION;

D O I：

10.1002/cctc.202101008

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

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 beta-substituted amines in good yield.

引用

页码：4520 / 4523

页数：4

共 27 条

[1] A rapid, sensitive colorimetric assay for the high-throughput screening of transaminases in liquid or solid-phase [J].

Baud, D. ;

Ladkau, N. ;

Moody, T. S. ;

Ward, J. M. ;

Hailes, H. C. .

CHEMICAL COMMUNICATIONS, 2015, 51 (97) :17225-17228

[2]

Benhamou L, 2019, GREEN CHEM, V21, P2035, DOI [10.1039/C9GC00448C, 10.1039/c9gc00448c]

[3]

Dunbabin A, 2017, GREEN CHEM, V19, P397, DOI [10.1039/c6gc02241c, 10.1039/C6GC02241C]

[4] ENANTIOSELECTIVE SYNTHESIS OF POLYFUNCTIONAL SMALL BUILDING-BLOCKS WITH A QUATERNARY STEREOGENIC CENTER [J].

ENDERS, D ;

ZAMPONI, A ;

SCHAFER, T ;

NUBLING, C ;

EICHENAUER, H ;

DEMIR, AS ;

RAABE, G .

CHEMISCHE BERICHTE, 1994, 127 (09) :1707-1721

[5] ENANTIOSELECTIVE SYNTHESIS OF BETA-SUBSTITUTED PRIMARY AMINES - ALPHA-ALKYLATION REDUCTIVE AMINATION OF ALDEHYDES VIA SAMP-HYDRAZONES [J].

ENDERS, D ;

SCHUBERT, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (05) :365-366

[6] ASYMMETRIC SYNTHESES VIA METALATED CHIRAL HYDRAZONES - OVERALL ENANTIOSELECTIVE ALPHA-ALKYLATION OF ACYCLIC KETONES [J].

ENDERS, D ;

EICHENAUER, H ;

BAUS, U ;

SCHUBERT, H ;

KREMER, KAM .

TETRAHEDRON, 1984, 40 (08) :1345-1359

[7]

Enders D., 1984, ANGEW CHEM, V96, P368

[8] Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses [J].

Foster, Robert W. ;

Tame, Christopher J. ;

Bucar, Dejan-Kresimir ;

Hailes, Helen C. ;

Sheppard, Tom D. .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (45) :15947-15950

[9] Synthesis of (R)- or (S)-valinol using ω-transaminases in aqueous and organic media [J].

Fuchs, Christine S. ;

Simon, Robert C. ;

Riethorst, Waander ;

Zepeck, Ferdinand ;

Kroutil, Wolfgang .

BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (20) :5558-5562

[10] ChemMatrix® for complex peptides and combinatorial chemistry [J].

Garcia-Ramos, Yesica ;

Paradis-Bas, Marta ;

Tulla-Puche, Judit ;

Albericio, Fernando .

JOURNAL OF PEPTIDE SCIENCE, 2010, 16 (12) :675-678

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