Self-assembly of small peptidomimetic cyclophanes

被引:68
作者
Becerril, J
Burguete, MI
Escuder, B [1 ]
Galindo, F
Gavara, R
Miravet, JF
Luis, SV
Peris, G
机构
[1] Univ Jaume 1, Dept Quim Inorgan & Organ, Castellon de La Plana 12071, Spain
[2] Univ Jaume 1, Serv Cent Instrumentacio Cien, Castellon de La Plana 12071, Spain
关键词
gels; helical structures; peptidomimetics; self-assembly; supramolecular chemistry;
D O I
10.1002/chem.200400031
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The self-assembly of a series of small peptidomimetic cyclophanes in organic solvents was studied. X-ray diffraction, NMR spectroscopy, and molecular modelling were used to understand the structural features of these self-assembling compounds both at the molecular and supramolecular level. The factors that could influence the formation of gels rather than crystals were studied and a model for the arrangement of molecules in the gel was proposed. Furthermore, scanning electron microscopy revealed that in some cases these compounds undergo a transcription of chirality when going from organogelator to helicoidal gel fibres.
引用
收藏
页码:3879 / 3890
页数:12
相关论文
共 110 条
[11]   Efficient macrocyclization of U-turn preorganized peptidomimetics:: The role of intramolecular H-bond and solvophobic effects [J].
Becerril, J ;
Bolte, M ;
Burguete, MI ;
Galindo, F ;
García-España, E ;
Luis, SV ;
Miravet, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6677-6686
[12]   Minimalist peptidomimetic cyclophanes as strong organogelators [J].
Becerril, J ;
Burguete, MI ;
Escuder, B ;
Luis, SV ;
Miravet, JF ;
Querol, M .
CHEMICAL COMMUNICATIONS, 2002, (07) :738-739
[13]   Exceptional adhesive and gelling properties of fibrous nanoscopic tapes of self-assembled bipolar urethane amides of L-phenylalanine [J].
Bhattacharya, S ;
Acharya, SNG ;
Raju, AR .
CHEMICAL COMMUNICATIONS, 1996, (17) :2101-2102
[14]   Impressive gelation in organic solvents by synthetic, low molecular mass, self-organizing urethane amides of L-phenylalanine [J].
Bhattacharya, S ;
Acharya, SNG .
CHEMISTRY OF MATERIALS, 1999, 11 (11) :3121-3132
[15]  
Biihler G., 2003, ANGEW CHEM, V115, P2599
[16]  
Bong D.T., 2001, ANGEW CHEMIE, V113, P2221
[17]  
*BRUK AN XRAY SYST, SAINT VERS 6 26
[18]   A metal-carbene carbohydrate amphiphile as a low-molecular-mass organometallic gelator [J].
Bühler, G ;
Feiters, MC ;
Nolte, RJM ;
Dötz, KH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (22) :2494-2497
[19]  
CALRIDGE TDW, 1999, HIGH RESOLUTION NMR
[20]   Hydrazinoazadipeptides as aromatic solvent gelators [J].
Carré, A ;
Le Grel, P ;
Baudy-Floc'h, M .
TETRAHEDRON LETTERS, 2001, 42 (10) :1887-1889