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Titolo:
Chiral discrimination of fructo-oligosaccharides toward amino acid derivatives by induced-fitting chiral recognition
Autore:
Shizuma, M; Adachi, H; Kawamura, M; Takai, Y; Takeda, T; Sawada, M;
Indirizzi:
Osaka Univ, Inst Sci & Ind Res, Ctr Mat Anal, Osaka 5670047, Japan Osaka Univ Osaka Japan 5670047 d Res, Ctr Mat Anal, Osaka 5670047, Japan Osaka Kyoiku Univ, Dept Biol, Osaka 5828582, Japan Osaka Kyoiku Univ Osaka Japan 5828582 v, Dept Biol, Osaka 5828582, Japan Osaka Univ, Fac Sci, Osaka 5600043, Japan Osaka Univ Osaka Japan 5600043Osaka Univ, Fac Sci, Osaka 5600043, Japan Osaka Municipal Tech Res Inst, Joto Ku, Osaka 5368553, Japan Osaka Municipal Tech Res Inst Osaka Japan 5368553 , Osaka 5368553, Japan
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
fascicolo: 4, , anno: 2001,
pagine: 592 - 601
SICI:
1472-779X(200104):4<592:CDOFTA>2.0.ZU;2-D
Fonte:
ISI
Lingua:
ENG
Soggetto:
HOST-GUEST COMPLEXATION; BOMBARDMENT MASS-SPECTROMETRY; LIQUID-CHROMATOGRAPHIC SEPARATION; OXIDE OLIGOMER COMPLEXES; ALKALI-METAL ION; CAPILLARY ZONE ELECTROPHORESIS; MICELLE SIZE DISTRIBUTION; CROWN-ETHERS; STATIONARY PHASES; ESTER SALTS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
88
Recensione:
Indirizzi per estratti:
Indirizzo: Shizuma, M Osaka Univ, Inst Sci & Ind Res, Ctr Mat Anal, Osaka 5670047, Japan Osaka Univ Osaka Japan 5670047 Mat Anal, Osaka 5670047, Japan
Citazione:
M. Shizuma et al., "Chiral discrimination of fructo-oligosaccharides toward amino acid derivatives by induced-fitting chiral recognition", J CHEM S P2, (4), 2001, pp. 592-601

Abstract

Among linear permethylated fructo-oligosaccharides containing various monosaccharide moieties at the reducing terminal, MeSorFru(3), MeGlc(6)Fru(3), and MeFruNys showed high degrees of enantioselectivity toward binding some amino acid 2-propyl ester salts. In particular MeFruNys indicated remarkable chiral discrimination toward [ValOPr(i)](+) (I-R/IS-Dn = 0.14 corresponding to -Delta DeltaG(enan) = 1.2 kcal mol(-1), S-selectivity) and [PheOPr(i)](+) (I-R/IS-Dn = 0.18 corresponding to -Delta DeltaG(enan) = 1.0 kcal mol(-1), S-selectivity). The results of FAB mass, UV-visible spectrometries, thermodynamic parameters, and NMR induced shifts provided evidence for the chiral discrimination of MeFruNys toward amino acid ester salts in the "induced-fitting chiral recognition system": the conformation of MeFruNys drastically changes from a linear to a pseudo-ring structure with a given cation such as a chiral organic ammonium ion or an alkali metallic ion. This is thefirst example of chiral discrimination of linear oligosaccharide derivatives toward amino acid derivatives based on the induced-fitting chiral recognition mechanism.

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Documento generato il 27/09/20 alle ore 04:35:51