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- W2080394158 abstract "A series of optically active 1,1′-binaphthalene-derived receptors with N-(pyridine-2,6-diyl)acetamide [CONH(py)] H-bonding sites in the 6,6′-positions has been prepared for the enantioselective complexation of the N-carbobenzyloxy (Cbz)-protected excitatory amino acids aspartic (Asp) and glutamic (Glu) acid via two COOH· · ·CONH(py) H-bonding arrays and additional secondary bonding interactions. The conformational homogeneity of the receptors is enhanced by locking the dihedral angle θ about the chirality axis through the C(1)–C(1′) bond of the 1,1′-binaphthalene moiety either by bridging the 2,2′-positions or by attaching bulky substituents to these centres. Computer modelling has shown that bridging is more efficient in locking this dihedral angle than the introduction of bulky substituents, and these predictions have been confirmed by 1H NMR binding studies in CDCl3 and in CDCl3–CD3OD 99.8∶0.2. Plots of the enantioselectivity Δ(ΔG°) (difference in stability between diastereoisomeric complexes) in the recognition by the bridged receptors as a function of the enforced dihedral angle θ are peak-shaped, and the highest values have been measured in CDCl3 (300 K) for the complexation of the enantiomers of N-Cbz-Asp [Δ(ΔG°) = 6.9 kJ mol–1] and N-Cbz-Glu [Δ(ΔG°) = 5.2 kJ mol–1] by (R)-21 (θ = 86 ± 4°). The more stable diastereoisomeric complexes are highly structured, and tight host–guest bonding has been confirmed by the observation of up to five intermolecular NOEs. Enforcing the conformational homogeneity by bridging represents a new general principle for improving the chiral recognition potential of 1,1′-binaphthalene receptors." @default.
- W2080394158 created "2016-06-24" @default.
- W2080394158 creator A5027690239 @default.
- W2080394158 creator A5030744316 @default.
- W2080394158 creator A5064252894 @default.
- W2080394158 creator A5073481867 @default.
- W2080394158 date "1998-01-01" @default.
- W2080394158 modified "2023-10-16" @default.
- W2080394158 title "Geometrical optimisation of 1,1′-binaphthalene receptors for enantioselective molecular recognition of excitatory amino acid derivatives" @default.
- W2080394158 cites W1963637989 @default.
- W2080394158 cites W1963882104 @default.
- W2080394158 cites W1966032809 @default.
- W2080394158 cites W1966323125 @default.
- W2080394158 cites W1968846947 @default.
- W2080394158 cites W1970591439 @default.
- W2080394158 cites W1972695765 @default.
- W2080394158 cites W1973946055 @default.
- W2080394158 cites W1974569290 @default.
- W2080394158 cites W1978890358 @default.
- W2080394158 cites W1979978767 @default.
- W2080394158 cites W1980830165 @default.
- W2080394158 cites W1981338080 @default.
- W2080394158 cites W1982462350 @default.
- W2080394158 cites W1990047749 @default.
- W2080394158 cites W1997570175 @default.
- W2080394158 cites W1998525343 @default.
- W2080394158 cites W1999484243 @default.
- W2080394158 cites W2003600067 @default.
- W2080394158 cites W2003990152 @default.
- W2080394158 cites W2006217691 @default.
- W2080394158 cites W2007434121 @default.
- W2080394158 cites W2010810483 @default.
- W2080394158 cites W2014841756 @default.
- W2080394158 cites W2015311060 @default.
- W2080394158 cites W2017053199 @default.
- W2080394158 cites W2017694805 @default.
- W2080394158 cites W2018014684 @default.
- W2080394158 cites W2019208078 @default.
- W2080394158 cites W2021180390 @default.
- W2080394158 cites W2025267195 @default.
- W2080394158 cites W2026286914 @default.
- W2080394158 cites W2027589723 @default.
- W2080394158 cites W2027657812 @default.
- W2080394158 cites W2031778882 @default.
- W2080394158 cites W2032379134 @default.
- W2080394158 cites W2033194645 @default.
- W2080394158 cites W2035407643 @default.
- W2080394158 cites W2037498916 @default.
- W2080394158 cites W2037849444 @default.
- W2080394158 cites W2038336928 @default.
- W2080394158 cites W2041189078 @default.
- W2080394158 cites W2041347298 @default.
- W2080394158 cites W2043248951 @default.
- W2080394158 cites W2044138435 @default.
- W2080394158 cites W2045096607 @default.
- W2080394158 cites W2047202866 @default.
- W2080394158 cites W2047730466 @default.
- W2080394158 cites W2048350795 @default.
- W2080394158 cites W2051976898 @default.
- W2080394158 cites W2053732437 @default.
- W2080394158 cites W2056417733 @default.
- W2080394158 cites W2057091413 @default.
- W2080394158 cites W2057220750 @default.
- W2080394158 cites W2057754641 @default.
- W2080394158 cites W2063512060 @default.
- W2080394158 cites W2064835714 @default.
- W2080394158 cites W2065150498 @default.
- W2080394158 cites W2068802098 @default.
- W2080394158 cites W2069595771 @default.
- W2080394158 cites W2070384235 @default.
- W2080394158 cites W2071360944 @default.
- W2080394158 cites W2071420013 @default.
- W2080394158 cites W2074048747 @default.
- W2080394158 cites W2074299636 @default.
- W2080394158 cites W2076083203 @default.
- W2080394158 cites W2076169614 @default.
- W2080394158 cites W2080311720 @default.
- W2080394158 cites W2081057108 @default.
- W2080394158 cites W2081377598 @default.
- W2080394158 cites W2082464318 @default.
- W2080394158 cites W2086461965 @default.
- W2080394158 cites W2088101998 @default.
- W2080394158 cites W2090035433 @default.
- W2080394158 cites W2091504308 @default.
- W2080394158 cites W2092427988 @default.
- W2080394158 cites W2093927445 @default.
- W2080394158 cites W2097413748 @default.
- W2080394158 cites W2097858708 @default.
- W2080394158 cites W2104483138 @default.
- W2080394158 cites W2125681770 @default.
- W2080394158 cites W2131124255 @default.
- W2080394158 cites W2151436915 @default.
- W2080394158 cites W2198205683 @default.
- W2080394158 cites W2241436162 @default.
- W2080394158 cites W2314755456 @default.
- W2080394158 cites W2361159576 @default.
- W2080394158 cites W2949273462 @default.
- W2080394158 cites W2951047158 @default.