Absolute stereochemical determination of chiral carboxylates using an achiral molecular tweezer

Hongsik Yoon, Chi Hwa Lee, Woo Dong Jang

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

A new type of molecular tweezer (1) has been synthesized for the direct determination of the absolute configuration of chiral carboxylates without analyte derivatization. Upon the addition of diamine and anionic guests, 1 exhibited shifts in its absorption spectrum with clear isosbestic points. The continuous variation method indicated that both the diamine and anionic guests form 1:1 host-guest complexes with 1 with very high binding affinity. When Boc-L-Ala (BLA) as a form of tetrabutylammonium salt was added to 1, a weak negative CD signal was observed. This weak CD signal was dramatically changed to a strong positive CD couplet upon addition of achiral 1,12-diaminododecane. Such a positive CD couplet was observed for all of the tested L-amino acid derivatives, while the D-amino acid derivatives gave the opposite signals. As a result of these unique characteristics of 1, it can be utilized as a highly sensitive probe for the absolute stereochemical determination of chiral carboxylates.

Original languageEnglish
Pages (from-to)12479-12486
Number of pages8
JournalChemistry - A European Journal
Volume18
Issue number39
DOIs
Publication statusPublished - 2012 Sep 24

Fingerprint

Diamines
Amino acids
Derivatives
Amino Acids
Absorption spectra
Salts
1,12-dodecamethylenediamine
tetrabutylammonium

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

@article{e8f4673679f74640a9693196dc345162,
title = "Absolute stereochemical determination of chiral carboxylates using an achiral molecular tweezer",
abstract = "A new type of molecular tweezer (1) has been synthesized for the direct determination of the absolute configuration of chiral carboxylates without analyte derivatization. Upon the addition of diamine and anionic guests, 1 exhibited shifts in its absorption spectrum with clear isosbestic points. The continuous variation method indicated that both the diamine and anionic guests form 1:1 host-guest complexes with 1 with very high binding affinity. When Boc-L-Ala (BLA) as a form of tetrabutylammonium salt was added to 1, a weak negative CD signal was observed. This weak CD signal was dramatically changed to a strong positive CD couplet upon addition of achiral 1,12-diaminododecane. Such a positive CD couplet was observed for all of the tested L-amino acid derivatives, while the D-amino acid derivatives gave the opposite signals. As a result of these unique characteristics of 1, it can be utilized as a highly sensitive probe for the absolute stereochemical determination of chiral carboxylates.",
author = "Hongsik Yoon and Lee, {Chi Hwa} and Jang, {Woo Dong}",
year = "2012",
month = "9",
day = "24",
doi = "10.1002/chem.201200371",
language = "English",
volume = "18",
pages = "12479--12486",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "39",

}

Absolute stereochemical determination of chiral carboxylates using an achiral molecular tweezer. / Yoon, Hongsik; Lee, Chi Hwa; Jang, Woo Dong.

In: Chemistry - A European Journal, Vol. 18, No. 39, 24.09.2012, p. 12479-12486.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Absolute stereochemical determination of chiral carboxylates using an achiral molecular tweezer

AU - Yoon, Hongsik

AU - Lee, Chi Hwa

AU - Jang, Woo Dong

PY - 2012/9/24

Y1 - 2012/9/24

N2 - A new type of molecular tweezer (1) has been synthesized for the direct determination of the absolute configuration of chiral carboxylates without analyte derivatization. Upon the addition of diamine and anionic guests, 1 exhibited shifts in its absorption spectrum with clear isosbestic points. The continuous variation method indicated that both the diamine and anionic guests form 1:1 host-guest complexes with 1 with very high binding affinity. When Boc-L-Ala (BLA) as a form of tetrabutylammonium salt was added to 1, a weak negative CD signal was observed. This weak CD signal was dramatically changed to a strong positive CD couplet upon addition of achiral 1,12-diaminododecane. Such a positive CD couplet was observed for all of the tested L-amino acid derivatives, while the D-amino acid derivatives gave the opposite signals. As a result of these unique characteristics of 1, it can be utilized as a highly sensitive probe for the absolute stereochemical determination of chiral carboxylates.

AB - A new type of molecular tweezer (1) has been synthesized for the direct determination of the absolute configuration of chiral carboxylates without analyte derivatization. Upon the addition of diamine and anionic guests, 1 exhibited shifts in its absorption spectrum with clear isosbestic points. The continuous variation method indicated that both the diamine and anionic guests form 1:1 host-guest complexes with 1 with very high binding affinity. When Boc-L-Ala (BLA) as a form of tetrabutylammonium salt was added to 1, a weak negative CD signal was observed. This weak CD signal was dramatically changed to a strong positive CD couplet upon addition of achiral 1,12-diaminododecane. Such a positive CD couplet was observed for all of the tested L-amino acid derivatives, while the D-amino acid derivatives gave the opposite signals. As a result of these unique characteristics of 1, it can be utilized as a highly sensitive probe for the absolute stereochemical determination of chiral carboxylates.

UR - http://www.scopus.com/inward/record.url?scp=84866390169&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84866390169&partnerID=8YFLogxK

U2 - 10.1002/chem.201200371

DO - 10.1002/chem.201200371

M3 - Article

C2 - 22907920

AN - SCOPUS:84866390169

VL - 18

SP - 12479

EP - 12486

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 39

ER -