Enantioselective Complexation of Flexible and Rigid Substrates through Molecular Recognition

Michael Famulok, Kyu‐Sung ‐S Jeong, Ghislain Deslongchamps, Julius Rebek

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Up to four hydrogen bonds are formed on complexation of hydantoins by 2,7‐naphthyl‐bridged dilactams. The L‐hydantoins (R may be CH2Ph, and CH(CH3)2, for example) bind preferentially to the (–)‐enantiomer of the receptor (ΔΔG = −0.6 kcal mol−1). Similarly, this enantioselectivity is observed in the complexation of L‐hydroorotic acid methyl ester. The selectivity of the binding of dipeptides, which are substantially more flexible, is less pronounced. (Figure Presented.)

Original languageEnglish
Pages (from-to)858-860
Number of pages3
JournalAngewandte Chemie International Edition in English
Volume30
Issue number7
DOIs
Publication statusPublished - 1991 Jul

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Molecular recognition
Complexation
Hydantoins
Enantiomers
Dipeptides
Enantioselectivity
Substrates
Esters
Hydrogen bonds
Acids

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

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abstract = "Up to four hydrogen bonds are formed on complexation of hydantoins by 2,7‐naphthyl‐bridged dilactams. The L‐hydantoins (R may be CH2Ph, and CH(CH3)2, for example) bind preferentially to the (–)‐enantiomer of the receptor (ΔΔG = −0.6 kcal mol−1). Similarly, this enantioselectivity is observed in the complexation of L‐hydroorotic acid methyl ester. The selectivity of the binding of dipeptides, which are substantially more flexible, is less pronounced. (Figure Presented.)",
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Enantioselective Complexation of Flexible and Rigid Substrates through Molecular Recognition. / Famulok, Michael; Jeong, Kyu‐Sung ‐S; Deslongchamps, Ghislain; Rebek, Julius.

In: Angewandte Chemie International Edition in English, Vol. 30, No. 7, 07.1991, p. 858-860.

Research output: Contribution to journalArticle

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