Learning from b12 enzymes: Biomimetic and bioinspired catalysts for eco-friendly organic synthesis

Keishiro Tahara, Ling Pan, Toshikazu Ono, Yoshio Hisaeda

Research output: Contribution to journalReview article

6 Citations (Scopus)

Abstract

Cobalamins (B12) play various important roles in vivo. Most B12-dependent enzymes are divided into three main subfamilies: adenosylcobalamin-dependent isomerases, methylcobalamin-dependent methyltransferases, and dehalogenases. Mimicking these B12 enzyme functions under non-enzymatic conditions offers good understanding of their elaborate reaction mechanisms. Furthermore, bio-inspiration offers a new approach to catalytic design for green and eco-friendly molecular transformations. As part of a study based on vitamin B12 derivatives including heptamethyl cobyrinate perchlorate, we describe biomimetic and bioinspired catalytic reactions with B12 enzyme functions. The reactions are classified according to the corresponding three B12 enzyme subfamilies, with a focus on our recent development on electrochemical and photochemical catalytic systems. Other important reactions are also described, with a focus on radical-involved reactions in terms of organic synthesis.

Original languageEnglish
Pages (from-to)2553-2567
Number of pages15
JournalBeilstein Journal of Organic Chemistry
Volume14
DOIs
Publication statusPublished - Oct 2 2018

Fingerprint

Biomimetics
Catalysts
Enzymes
Vitamin B 12
Isomerases
Methyltransferases
Derivatives

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Learning from b12 enzymes : Biomimetic and bioinspired catalysts for eco-friendly organic synthesis. / Tahara, Keishiro; Pan, Ling; Ono, Toshikazu; Hisaeda, Yoshio.

In: Beilstein Journal of Organic Chemistry, Vol. 14, 02.10.2018, p. 2553-2567.

Research output: Contribution to journalReview article

@article{ce2c1983361f4938bac85825aa56d1a0,
title = "Learning from b12 enzymes: Biomimetic and bioinspired catalysts for eco-friendly organic synthesis",
abstract = "Cobalamins (B12) play various important roles in vivo. Most B12-dependent enzymes are divided into three main subfamilies: adenosylcobalamin-dependent isomerases, methylcobalamin-dependent methyltransferases, and dehalogenases. Mimicking these B12 enzyme functions under non-enzymatic conditions offers good understanding of their elaborate reaction mechanisms. Furthermore, bio-inspiration offers a new approach to catalytic design for green and eco-friendly molecular transformations. As part of a study based on vitamin B12 derivatives including heptamethyl cobyrinate perchlorate, we describe biomimetic and bioinspired catalytic reactions with B12 enzyme functions. The reactions are classified according to the corresponding three B12 enzyme subfamilies, with a focus on our recent development on electrochemical and photochemical catalytic systems. Other important reactions are also described, with a focus on radical-involved reactions in terms of organic synthesis.",
author = "Keishiro Tahara and Ling Pan and Toshikazu Ono and Yoshio Hisaeda",
year = "2018",
month = "10",
day = "2",
doi = "10.3762/bjoc.14.232",
language = "English",
volume = "14",
pages = "2553--2567",
journal = "Beilstein Journal of Organic Chemistry",
issn = "1860-5397",
publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

TY - JOUR

T1 - Learning from b12 enzymes

T2 - Biomimetic and bioinspired catalysts for eco-friendly organic synthesis

AU - Tahara, Keishiro

AU - Pan, Ling

AU - Ono, Toshikazu

AU - Hisaeda, Yoshio

PY - 2018/10/2

Y1 - 2018/10/2

N2 - Cobalamins (B12) play various important roles in vivo. Most B12-dependent enzymes are divided into three main subfamilies: adenosylcobalamin-dependent isomerases, methylcobalamin-dependent methyltransferases, and dehalogenases. Mimicking these B12 enzyme functions under non-enzymatic conditions offers good understanding of their elaborate reaction mechanisms. Furthermore, bio-inspiration offers a new approach to catalytic design for green and eco-friendly molecular transformations. As part of a study based on vitamin B12 derivatives including heptamethyl cobyrinate perchlorate, we describe biomimetic and bioinspired catalytic reactions with B12 enzyme functions. The reactions are classified according to the corresponding three B12 enzyme subfamilies, with a focus on our recent development on electrochemical and photochemical catalytic systems. Other important reactions are also described, with a focus on radical-involved reactions in terms of organic synthesis.

AB - Cobalamins (B12) play various important roles in vivo. Most B12-dependent enzymes are divided into three main subfamilies: adenosylcobalamin-dependent isomerases, methylcobalamin-dependent methyltransferases, and dehalogenases. Mimicking these B12 enzyme functions under non-enzymatic conditions offers good understanding of their elaborate reaction mechanisms. Furthermore, bio-inspiration offers a new approach to catalytic design for green and eco-friendly molecular transformations. As part of a study based on vitamin B12 derivatives including heptamethyl cobyrinate perchlorate, we describe biomimetic and bioinspired catalytic reactions with B12 enzyme functions. The reactions are classified according to the corresponding three B12 enzyme subfamilies, with a focus on our recent development on electrochemical and photochemical catalytic systems. Other important reactions are also described, with a focus on radical-involved reactions in terms of organic synthesis.

UR - http://www.scopus.com/inward/record.url?scp=85054835654&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85054835654&partnerID=8YFLogxK

U2 - 10.3762/bjoc.14.232

DO - 10.3762/bjoc.14.232

M3 - Review article

AN - SCOPUS:85054835654

VL - 14

SP - 2553

EP - 2567

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -