Asymmetric sulfoxidation and amine binding by H64D/V68A and H64D/V68S Mb: Mechanistic insight into the chiral discrimination step

Shigeru Kato; Hui Jun Yang; Takafumi Ueno; Shin ichi Ozaki; George N. Phillips; Shunichi Fukuzumi; Yoshihito Watanabe

doi:10.1021/ja0256414

Asymmetric sulfoxidation and amine binding by H64D/V68A and H64D/V68S Mb: Mechanistic insight into the chiral discrimination step

Shigeru Kato
, Hui Jun Yang
, Takafumi Ueno
, Shin ichi Ozaki
, George N. Phillips
, Shunichi Fukuzumi
, Yoshihito Watanabe

Department of Chemistry & Nanoscience

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

36 Scopus citations

Abstract

The H64D/V68A and H64D/V68S mutants of Myoglobin are found to oxidize thioanisole with high enantioselectivity and reactivity. These mutants are also capable of enantioselective binding of α-methylbenzylamine, which mimics an expected sulfoxidation intermediate. The kinetic study of the amine binding shows that the Fe-O bond cleavage in the intermediate may be the chiral discrimination step of the sulfoxidation.

Original language	English
Pages (from-to)	8506-8507
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	124
Issue number	29
DOIs	https://doi.org/10.1021/ja0256414
State	Published - 24 Jul 2002

Access to Document

10.1021/ja0256414

Cite this

@article{c6874ad052894de38a132100cca26627,

title = "Asymmetric sulfoxidation and amine binding by H64D/V68A and H64D/V68S Mb: Mechanistic insight into the chiral discrimination step",

abstract = "The H64D/V68A and H64D/V68S mutants of Myoglobin are found to oxidize thioanisole with high enantioselectivity and reactivity. These mutants are also capable of enantioselective binding of α-methylbenzylamine, which mimics an expected sulfoxidation intermediate. The kinetic study of the amine binding shows that the Fe-O bond cleavage in the intermediate may be the chiral discrimination step of the sulfoxidation.",

author = "Shigeru Kato and Yang, \{Hui Jun\} and Takafumi Ueno and Ozaki, \{Shin ichi\} and Phillips, \{George N.\} and Shunichi Fukuzumi and Yoshihito Watanabe",

year = "2002",

month = jul,

day = "24",

doi = "10.1021/ja0256414",

language = "English",

volume = "124",

pages = "8506--8507",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "29",

}

TY - JOUR

T1 - Asymmetric sulfoxidation and amine binding by H64D/V68A and H64D/V68S Mb

T2 - Mechanistic insight into the chiral discrimination step

AU - Kato, Shigeru

AU - Yang, Hui Jun

AU - Ueno, Takafumi

AU - Ozaki, Shin ichi

AU - Phillips, George N.

AU - Fukuzumi, Shunichi

AU - Watanabe, Yoshihito

PY - 2002/7/24

Y1 - 2002/7/24

N2 - The H64D/V68A and H64D/V68S mutants of Myoglobin are found to oxidize thioanisole with high enantioselectivity and reactivity. These mutants are also capable of enantioselective binding of α-methylbenzylamine, which mimics an expected sulfoxidation intermediate. The kinetic study of the amine binding shows that the Fe-O bond cleavage in the intermediate may be the chiral discrimination step of the sulfoxidation.

AB - The H64D/V68A and H64D/V68S mutants of Myoglobin are found to oxidize thioanisole with high enantioselectivity and reactivity. These mutants are also capable of enantioselective binding of α-methylbenzylamine, which mimics an expected sulfoxidation intermediate. The kinetic study of the amine binding shows that the Fe-O bond cleavage in the intermediate may be the chiral discrimination step of the sulfoxidation.

UR - https://www.scopus.com/pages/publications/0037166981

U2 - 10.1021/ja0256414

DO - 10.1021/ja0256414

M3 - Article

C2 - 12121073

AN - SCOPUS:0037166981

SN - 0002-7863

VL - 124

SP - 8506

EP - 8507

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 29

ER -

Asymmetric sulfoxidation and amine binding by H64D/V68A and H64D/V68S Mb: Mechanistic insight into the chiral discrimination step

Abstract

Access to Document

Fingerprint

Cite this