Chiral recognition and supramolecular photoreaction of 1,1'-binaphthol with bovine and human serum albumins

Masaki Nishijima; Jae Won Chang; Cheng Yang; Gaku Fukuhara; Tadashi Mori; Yoshihisa Inoue

doi:10.1007/s11164-012-0655-1

Chiral recognition and supramolecular photoreaction of 1,1'-binaphthol with bovine and human serum albumins

Masaki Nishijima, Jae Won Chang, Cheng Yang, Gaku Fukuhara, Tadashi Mori, Yoshihisa Inoue

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

14 Citations (Scopus)

Abstract

In their pioneering study in 1991, Levi-Minzi and Zandomeneghi discovered that photoirradiation of racemic 1,1'-binaphthol (rac-1) in the presence of bovine serum albumin (BSA) in distilled water gave (R)-1 in 99 % enantiomeric excess (ee) after 77 % of the starting material had been consumed. No similar attempt was made with human serum albumin (HSA). In this study of the effects of phosphate buffer solution on the ground-state affinity and excited-state photobehavior of 1 with serum albumin we found that both BSA and HSA preferentially bind the (S) enantiomer of 1 and that photoreaction of rac-1 mediated by BSA and HSA affords (R)-1 in 98 % ee with 99 % conversion and in 46 % ee with 65 % conversion, respectively.

Original language	English
Pages (from-to)	371-383
Number of pages	13
Journal	Research on Chemical Intermediates
Volume	39
Issue number	1
DOIs	https://doi.org/10.1007/s11164-012-0655-1
Publication status	Published - 2013 Jan
Externally published	Yes

Keywords

Binaphthol
Chiral photochemistry
Serum albumin
Supramolecular photochirogenesis

ASJC Scopus subject areas

Chemistry(all)

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10.1007/s11164-012-0655-1

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title = "Chiral recognition and supramolecular photoreaction of 1,1'-binaphthol with bovine and human serum albumins",

abstract = "In their pioneering study in 1991, Levi-Minzi and Zandomeneghi discovered that photoirradiation of racemic 1,1'-binaphthol (rac-1) in the presence of bovine serum albumin (BSA) in distilled water gave (R)-1 in 99 % enantiomeric excess (ee) after 77 % of the starting material had been consumed. No similar attempt was made with human serum albumin (HSA). In this study of the effects of phosphate buffer solution on the ground-state affinity and excited-state photobehavior of 1 with serum albumin we found that both BSA and HSA preferentially bind the (S) enantiomer of 1 and that photoreaction of rac-1 mediated by BSA and HSA affords (R)-1 in 98 % ee with 99 % conversion and in 46 % ee with 65 % conversion, respectively.",

keywords = "Binaphthol, Chiral photochemistry, Serum albumin, Supramolecular photochirogenesis",

author = "Masaki Nishijima and Chang, {Jae Won} and Cheng Yang and Gaku Fukuhara and Tadashi Mori and Yoshihisa Inoue",

note = "Funding Information: Acknowledgments This work was supported by a Grant-in-Aid for Scientific Research (A) (no. 21245011; YI) and (B) (no. 23350018; TM) from the Japan Society for the Promotion of Science, and a Grant for Basic Science Research from The Sumitomo Foundation (no. 080435; MN), which are gratefully acknowledged.",

year = "2013",

month = jan,

doi = "10.1007/s11164-012-0655-1",

language = "English",

volume = "39",

pages = "371--383",

journal = "Research on Chemical Intermediates",

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AU - Nishijima, Masaki

AU - Chang, Jae Won

AU - Yang, Cheng

AU - Fukuhara, Gaku

AU - Mori, Tadashi

AU - Inoue, Yoshihisa

N1 - Funding Information: Acknowledgments This work was supported by a Grant-in-Aid for Scientific Research (A) (no. 21245011; YI) and (B) (no. 23350018; TM) from the Japan Society for the Promotion of Science, and a Grant for Basic Science Research from The Sumitomo Foundation (no. 080435; MN), which are gratefully acknowledged.

PY - 2013/1

Y1 - 2013/1

N2 - In their pioneering study in 1991, Levi-Minzi and Zandomeneghi discovered that photoirradiation of racemic 1,1'-binaphthol (rac-1) in the presence of bovine serum albumin (BSA) in distilled water gave (R)-1 in 99 % enantiomeric excess (ee) after 77 % of the starting material had been consumed. No similar attempt was made with human serum albumin (HSA). In this study of the effects of phosphate buffer solution on the ground-state affinity and excited-state photobehavior of 1 with serum albumin we found that both BSA and HSA preferentially bind the (S) enantiomer of 1 and that photoreaction of rac-1 mediated by BSA and HSA affords (R)-1 in 98 % ee with 99 % conversion and in 46 % ee with 65 % conversion, respectively.

AB - In their pioneering study in 1991, Levi-Minzi and Zandomeneghi discovered that photoirradiation of racemic 1,1'-binaphthol (rac-1) in the presence of bovine serum albumin (BSA) in distilled water gave (R)-1 in 99 % enantiomeric excess (ee) after 77 % of the starting material had been consumed. No similar attempt was made with human serum albumin (HSA). In this study of the effects of phosphate buffer solution on the ground-state affinity and excited-state photobehavior of 1 with serum albumin we found that both BSA and HSA preferentially bind the (S) enantiomer of 1 and that photoreaction of rac-1 mediated by BSA and HSA affords (R)-1 in 98 % ee with 99 % conversion and in 46 % ee with 65 % conversion, respectively.

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KW - Chiral photochemistry

KW - Serum albumin

KW - Supramolecular photochirogenesis

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Chiral recognition and supramolecular photoreaction of 1,1'-binaphthol with bovine and human serum albumins

Abstract

Keywords

ASJC Scopus subject areas

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