N-Alkyl-α-amino acids in Nature and their biocatalytic preparation

Julia F. Hyslop; Sarah L. Lovelock; Allan J. B. Watson; Peter W. Sutton; Gheorghe-Doru Roiban

doi:10.1016/j.jbiotec.2019.01.006

N-Alkyl-α-amino acids in Nature and their biocatalytic preparation

Julia F. Hyslop, Sarah L. Lovelock, Allan J. B. Watson, Peter W. Sutton, Gheorghe-Doru Roiban

School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

N-alkylated-α-amino acids are useful building blocks for the pharmaceutical and fine chemical industries. Enantioselective methods of N-alkylated-α-amino acid synthesis are therefore highly valuable and widely investigated. While there are a variety of chemical methods for their synthesis, they often employ stoichiometric quantities of hazardous reagents such as pyrophoric metal hydrides or genotoxic alkylating agents, whereas biocatalytic routes can provide a greener and cleaner alternative to existing methods. This review highlights the occurrence of the N-alkyl-α-amino acid motif and its role in nature, important applications towards human health and biocatalytic methods of preparation. Several enzyme classes that can be used to access chiral N-alkylated-α-amino acids and their substrate selectivities are detailed.

Original language	English
Pages (from-to)	56-65
Number of pages	10
Journal	Journal of Biotechnology
Volume	293
Early online date	26 Jan 2019
DOIs	https://doi.org/10.1016/j.jbiotec.2019.01.006
Publication status	Published - 10 Mar 2019

Keywords

N-Alkyl-α-amino acids
Biocatalysis
N-Methyl transferases
Dehydrogenases

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.jbiotec.2019.01.006

Hyslop_2019_JB_nature_AAM
Copyright © 2019 Elsevier B.V. All rights reserved. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1016/j.jbiotec.2019.01.006
Accepted author manuscript, 746 KBLicence: CC BY-NC-ND

Cite this

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title = "N-Alkyl-α-amino acids in Nature and their biocatalytic preparation",

abstract = "N-alkylated-α-amino acids are useful building blocks for the pharmaceutical and fine chemical industries. Enantioselective methods of N-alkylated-α-amino acid synthesis are therefore highly valuable and widely investigated. While there are a variety of chemical methods for their synthesis, they often employ stoichiometric quantities of hazardous reagents such as pyrophoric metal hydrides or genotoxic alkylating agents, whereas biocatalytic routes can provide a greener and cleaner alternative to existing methods. This review highlights the occurrence of the N-alkyl-α-amino acid motif and its role in nature, important applications towards human health and biocatalytic methods of preparation. Several enzyme classes that can be used to access chiral N-alkylated-α-amino acids and their substrate selectivities are detailed.",

keywords = "N-Alkyl-α-amino acids, Biocatalysis, N-Methyl transferases, Dehydrogenases",

author = "Hyslop, {Julia F.} and Lovelock, {Sarah L.} and Watson, {Allan J. B.} and Sutton, {Peter W.} and Gheorghe-Doru Roiban",

note = "PWS would like to acknowledge the European Union for his current funding: “This project has received funding from the European Union{\textquoteright}s Horizon 2020 research and innovation programme under Marie Sk{\l}odowska-Curie grant agreement No 665919”.",

year = "2019",

month = mar,

day = "10",

doi = "10.1016/j.jbiotec.2019.01.006",

language = "English",

volume = "293",

pages = "56--65",

journal = "Journal of Biotechnology",

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TY - JOUR

T1 - N-Alkyl-α-amino acids in Nature and their biocatalytic preparation

AU - Hyslop, Julia F.

AU - Lovelock, Sarah L.

AU - Watson, Allan J. B.

AU - Sutton, Peter W.

AU - Roiban, Gheorghe-Doru

N1 - PWS would like to acknowledge the European Union for his current funding: “This project has received funding from the European Union’s Horizon 2020 research and innovation programme under Marie Skłodowska-Curie grant agreement No 665919”.

PY - 2019/3/10

Y1 - 2019/3/10

N2 - N-alkylated-α-amino acids are useful building blocks for the pharmaceutical and fine chemical industries. Enantioselective methods of N-alkylated-α-amino acid synthesis are therefore highly valuable and widely investigated. While there are a variety of chemical methods for their synthesis, they often employ stoichiometric quantities of hazardous reagents such as pyrophoric metal hydrides or genotoxic alkylating agents, whereas biocatalytic routes can provide a greener and cleaner alternative to existing methods. This review highlights the occurrence of the N-alkyl-α-amino acid motif and its role in nature, important applications towards human health and biocatalytic methods of preparation. Several enzyme classes that can be used to access chiral N-alkylated-α-amino acids and their substrate selectivities are detailed.

AB - N-alkylated-α-amino acids are useful building blocks for the pharmaceutical and fine chemical industries. Enantioselective methods of N-alkylated-α-amino acid synthesis are therefore highly valuable and widely investigated. While there are a variety of chemical methods for their synthesis, they often employ stoichiometric quantities of hazardous reagents such as pyrophoric metal hydrides or genotoxic alkylating agents, whereas biocatalytic routes can provide a greener and cleaner alternative to existing methods. This review highlights the occurrence of the N-alkyl-α-amino acid motif and its role in nature, important applications towards human health and biocatalytic methods of preparation. Several enzyme classes that can be used to access chiral N-alkylated-α-amino acids and their substrate selectivities are detailed.

KW - N-Alkyl-α-amino acids

KW - Biocatalysis

KW - N-Methyl transferases

KW - Dehydrogenases

U2 - 10.1016/j.jbiotec.2019.01.006

DO - 10.1016/j.jbiotec.2019.01.006

M3 - Article

SN - 0168-1656

VL - 293

SP - 56

EP - 65

JO - Journal of Biotechnology

JF - Journal of Biotechnology

ER -

N-Alkyl-α-amino acids in Nature and their biocatalytic preparation

Abstract

Keywords

UN SDGs

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