Gas-phase enantioselectivity

被引:103
作者
Filippi, A
Giardini, A
Piccirillo, S
Speranza, M
机构
[1] Univ Roma La Sapienza, Dipartimento Studi Chim & Tecnol Sostanze Biol At, I-00185 Rome, Italy
[2] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy
[3] Univ Roma Tor Vergata, Dipartimento Sci & Tecnol Chim, Rome, Italy
关键词
gas-phase enantioselectivity; noncovalent interactions; mass spectrometry; radiolysis; resonance-enhanced multiphoton ionization time-of-flight (REMPI-TOF) spectroscopy;
D O I
10.1016/S1387-3806(00)00196-2
中图分类号
O64 [物理化学(理论化学)、化学物理学]; O56 [分子物理学、原子物理学];
学科分类号
070203 ; 070304 ; 081704 ; 1406 ;
摘要
Determination of the intrinsic noncovalent interactions governing chiral recognition in diastereomeric complexes constitutes the basis for understanding information transfer between molecules in living systems as well as in synthetic supramolecular structures. The most important experimental methodologies so far employed for this task are illustrated in the present review. Emphasis is put on the principles and the applications of techniques, such as radiolysis, Fourier transform ion cyclotron resonance (FTICR) and collision-induced dissociation (CID) mass spectrometry, and resonance-enhanced multiphoton ionization time-of-flight (REMPI-TOF) spectroscopy, that allow measurement of the relative stability of diastereomeric ion/molecule and molecule/molecule complexes and quantification of the short-range forces controlling their enantioselective evolution to products. (C) 2000 Elsevier Science B.V.
引用
收藏
页码:137 / 163
页数:27
相关论文
共 75 条
[11]   GAS-PHASE ACID-INDUCED RING-OPENING IN DIASTEREOISOMERIC 9,10-OXIDES DERIVED FROM TRANS-1,2,3,4,4A,10A-HEXAHYDROPHENANTHRENE [J].
CECCHI, P ;
CHINI, M ;
CROTTI, P ;
PIZZABIOCCA, A ;
RENZI, G ;
SPERANZA, M .
TETRAHEDRON, 1991, 47 (26) :4683-4692
[12]   SUBSTITUENT EFFECTS ON THE REGIOSELECTIVITY AND STEREOSELECTIVITY OF GAS-PHASE ACID-INDUCED RING-OPENING IN 1-ARYLCYCLOHEXENE OXIDES [J].
CECCHI, P ;
PIZZABIOCCA, A ;
RENZI, G ;
CHINI, M ;
CROTTI, P ;
MACCHIA, F ;
SPERANZA, M .
TETRAHEDRON, 1989, 45 (13) :4227-4234
[13]   AROMATIC SUBSTITUENT EFFECT ON THE STEREOSELECTIVITY OF THE GAS-PHASE ACID-INDUCED RING-OPENING IN 9,10-OXIDES DERIVED FROM TRANS-1,2,3,4,4A,10A-HEXAHYDROPHENANTHRENE [J].
CHINI, M ;
CROTTI, P ;
MINUTOLO, F ;
DEZI, E ;
LOMBARDOZZI, A ;
PIZZABIOCCA, A ;
RENZI, G .
TETRAHEDRON, 1993, 49 (26) :5845-5858
[14]   CHIRAL HOST-GUEST RECOGNITION IN AN ION-MOLECULE REACTION [J].
CHU, IH ;
DEARDEN, DV ;
BRADSHAW, JS ;
HUSZTHY, P ;
IZATT, RM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4318-4320
[15]   NAKED PROTEIN CONFORMATIONS - CYTOCHROME-C IN THE GAS-PHASE [J].
CLEMMER, DE ;
HUDGINS, RR ;
JARROLD, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (40) :10141-10142
[16]  
COOKS RG, 1994, MASS SPECTROM REV, V13, P287
[17]   GAS-PHASE ACID-INDUCED RING-OPENING OF AN ALPHA,BETA-EPOXYSILANE - THE 1ST CASE OF COMPLETE REGIOSELECTIVITY AND STEREOSELECTIVITY IN AN ION-MOLECULE REACTION IN THE GAS-PHASE [J].
CROTTI, P ;
MACCHIA, F ;
PIZZABIOCCA, A ;
RENZI, G ;
SPERANZA, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (06) :485-487
[18]   ANOMALOUS STEREOCHEMISTRY OF GAS-PHASE ACID-INDUCED RING-OPENING IN 1-PHENYLCYCLOHEXENE OXIDE [J].
CROTTI, P ;
MACCHIA, F ;
PIZZABIOCCA, A ;
RENZI, G ;
SPERANZA, M .
TETRAHEDRON LETTERS, 1987, 28 (29) :3393-3396
[19]  
CROTTI P, 1987, GAZZ CHIM ITAL, V117, P739
[20]   CHIRAL SELECTORS WITH CHELATING PROPERTIES IN LIQUID-CHROMATOGRAPHY - FUNDAMENTAL REFLECTIONS AND SELECTIVE REVIEW OF RECENT DEVELOPMENTS [J].
DAVANKOV, VA .
JOURNAL OF CHROMATOGRAPHY A, 1994, 666 (1-2) :55-76