Synthesis of novel H8-binaphthol-based chiral receptors and their applications in enantioselective recognition of 1,2-amino alcohols and chirality conversion of L-amino acids to D-amino acids

Hyein Jung; Raju Nandhakumar; Hoe Jin Yoon; Sang Gi Lee; Kwan Mook Kim

doi:10.5012/bkcs.2010.31.5.1289

Synthesis of novel H₈-binaphthol-based chiral receptors and their applications in enantioselective recognition of 1,2-amino alcohols and chirality conversion of L-amino acids to D-amino acids

Hyein Jung
, Raju Nandhakumar
, Hoe Jin Yoon
, Sang Gi Lee
, Kwan Mook Kim

Department of Chemistry & Nanoscience

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

5 Scopus citations

Abstract

Novel H₈-binaphthol-based chiral receptors appended with an uryl moiety (2a) and a guanidinium moiety (2b) have been designed and synthesized for the enantioselective recognition of 1,2-amino alcohols via reversible imine formation. The selectivities (K_R/K_S = 9.8 ̃ 19.4) of 2b in imine formation with 1,2-amino alcohols are higher than those of 2a (K_R/K_S = 1.8 ̃ 4.5). Similar efficiency trend have been observed in the conversion of L-amino acids to D-amino acids, i.e., the efficiency of the receptor 2b (D/L ratio: 4.3 ̃ 10.1) is superior to 2a (D/L ratio: 4.0 ̃ 8.7).

Original language	English
Pages (from-to)	1289-1294
Number of pages	6
Journal	Bulletin of the Korean Chemical Society
Volume	31
Issue number	5
DOIs	https://doi.org/10.5012/bkcs.2010.31.5.1289
State	Published - 20 May 2010

Keywords

Amino acid
Amino alcohol
Chirality conversion
Enantioselective recognition
Octahydrobinaphthol

Access to Document

10.5012/bkcs.2010.31.5.1289

Cite this

@article{700bb66e81724d728864cbfb85250d08,

title = "Synthesis of novel H8-binaphthol-based chiral receptors and their applications in enantioselective recognition of 1,2-amino alcohols and chirality conversion of L-amino acids to D-amino acids",

abstract = "Novel H8-binaphthol-based chiral receptors appended with an uryl moiety (2a) and a guanidinium moiety (2b) have been designed and synthesized for the enantioselective recognition of 1,2-amino alcohols via reversible imine formation. The selectivities (KR/KS = 9.8{\~ } 19.4) of 2b in imine formation with 1,2-amino alcohols are higher than those of 2a (KR/KS = 1.8{\~ } 4.5). Similar efficiency trend have been observed in the conversion of L-amino acids to D-amino acids, i.e., the efficiency of the receptor 2b (D/L ratio: 4.3{\~ } 10.1) is superior to 2a (D/L ratio: 4.0{\~ } 8.7).",

keywords = "Amino acid, Amino alcohol, Chirality conversion, Enantioselective recognition, Octahydrobinaphthol",

author = "Hyein Jung and Raju Nandhakumar and Yoon, \{Hoe Jin\} and Lee, \{Sang Gi\} and Kim, \{Kwan Mook\}",

year = "2010",

month = may,

day = "20",

doi = "10.5012/bkcs.2010.31.5.1289",

language = "English",

volume = "31",

pages = "1289--1294",

journal = "Bulletin of the Korean Chemical Society",

issn = "0253-2964",

publisher = "Wiley-Blackwell",

number = "5",

}

Synthesis of novel H₈-binaphthol-based chiral receptors and their applications in enantioselective recognition of 1,2-amino alcohols and chirality conversion of L-amino acids to D-amino acids. / Jung, Hyein; Nandhakumar, Raju; Yoon, Hoe Jin et al.
In: Bulletin of the Korean Chemical Society, Vol. 31, No. 5, 20.05.2010, p. 1289-1294.

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

TY - JOUR

T1 - Synthesis of novel H8-binaphthol-based chiral receptors and their applications in enantioselective recognition of 1,2-amino alcohols and chirality conversion of L-amino acids to D-amino acids

AU - Jung, Hyein

AU - Nandhakumar, Raju

AU - Yoon, Hoe Jin

AU - Lee, Sang Gi

AU - Kim, Kwan Mook

PY - 2010/5/20

Y1 - 2010/5/20

N2 - Novel H8-binaphthol-based chiral receptors appended with an uryl moiety (2a) and a guanidinium moiety (2b) have been designed and synthesized for the enantioselective recognition of 1,2-amino alcohols via reversible imine formation. The selectivities (KR/KS = 9.8 ̃ 19.4) of 2b in imine formation with 1,2-amino alcohols are higher than those of 2a (KR/KS = 1.8 ̃ 4.5). Similar efficiency trend have been observed in the conversion of L-amino acids to D-amino acids, i.e., the efficiency of the receptor 2b (D/L ratio: 4.3 ̃ 10.1) is superior to 2a (D/L ratio: 4.0 ̃ 8.7).

AB - Novel H8-binaphthol-based chiral receptors appended with an uryl moiety (2a) and a guanidinium moiety (2b) have been designed and synthesized for the enantioselective recognition of 1,2-amino alcohols via reversible imine formation. The selectivities (KR/KS = 9.8 ̃ 19.4) of 2b in imine formation with 1,2-amino alcohols are higher than those of 2a (KR/KS = 1.8 ̃ 4.5). Similar efficiency trend have been observed in the conversion of L-amino acids to D-amino acids, i.e., the efficiency of the receptor 2b (D/L ratio: 4.3 ̃ 10.1) is superior to 2a (D/L ratio: 4.0 ̃ 8.7).

KW - Amino acid

KW - Amino alcohol

KW - Chirality conversion

KW - Enantioselective recognition

KW - Octahydrobinaphthol

UR - https://www.scopus.com/pages/publications/77952643436

U2 - 10.5012/bkcs.2010.31.5.1289

DO - 10.5012/bkcs.2010.31.5.1289

M3 - Article

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SN - 0253-2964

VL - 31

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JO - Bulletin of the Korean Chemical Society

JF - Bulletin of the Korean Chemical Society

IS - 5