Deracemization of an axially chiral biphenylic derivative as a tool for investigating chiral recognition in self-assemblies

被引:32
作者
Borocci, S
Ceccacci, F
Galantini, L
Mancini, G
Monti, D
Scipioni, A
Venanzi, M
机构
[1] Univ Roma La Sapienza, Dipartimento Chim, CNR, ICCOM,Sez Roma, I-00185 Rome, Italy
[2] Univ Roma Tor Vergata, Dipartimento Sci & Tecnol Chim, Rome, Italy
关键词
atropisomer; organization; aggregates; cationic surfactant; diastereomer;
D O I
10.1002/chir.10230
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Two diastereomeric cationic surfactants derived from L-proline, in which the second chiral center is a quaternary nitrogen, have been separated and fully characterized. The recognition properties of the aggregates formed by the two diastereomeric surfactants have been investigated by circular dichroism and H-1 NMR through deracemization of racemic 2-carboxy-2'-dodecyloxy-6-nitrobiphenyl.
引用
收藏
页码:441 / 447
页数:7
相关论文
共 12 条
[1]   Micelle aggregation numbers of surfactants in aqueous solutions: A comparison between the results from steady-state and time-resolved fluorescence quenching [J].
Alargova, RG ;
Kochijashky, II ;
Sierra, ML ;
Zana, R .
LANGMUIR, 1998, 14 (19) :5412-5418
[2]   From parity to chirality:: chemical implications revisited [J].
Avalos, M ;
Babiano, R ;
Cintas, P ;
Jiménez, JL ;
Palacios, JC .
TETRAHEDRON-ASYMMETRY, 2000, 11 (14) :2845-2874
[3]  
Bales BL, 2002, J PHYS CHEM B, V106, P9033, DOI [10.1021/jp021297l, 10.1021/jp0212971]
[4]   Recognition in organized aggregates formed by a chiral amidic surfactant [J].
Bella, J ;
Borocci, S ;
Mancini, G .
LANGMUIR, 1999, 15 (23) :8025-8031
[5]   Deracemization of an axially chiral biphenylic structure in chiral micellar aggregates [J].
Borocci, S ;
Erba, M ;
Mancini, G ;
Scipioni, A .
LANGMUIR, 1998, 14 (08) :1960-1962
[7]   Interactions in aqueous systems containing sodium cholate/calcium chloride mixtures [J].
FilipovicVincekovic, N ;
BabicIvancic, V ;
Smit, I .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 1996, 177 (02) :646-657
[8]  
FUHRHOP JH, 1994, MONOGRAPHS SUPRAMOLE, P151
[9]   Determination of micellar aggregation numbers in dilute surfactant systems with the fluorescence quenching method. [J].
Hansson, P ;
Jönsson, B ;
Ström, C ;
Söderman, O .
JOURNAL OF PHYSICAL CHEMISTRY B, 2000, 104 (15) :3496-3506
[10]   APPLICATION OF PHASE SENSITIVE TWO-DIMENSIONAL CORRELATED SPECTROSCOPY (COSY) FOR MEASUREMENTS OF H-1-H-1 SPIN-SPIN COUPLING-CONSTANTS IN PROTEINS [J].
MARION, D ;
WUTHRICH, K .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1983, 113 (03) :967-974