Carlos Cativiela *

Autor invitado por SIIC

SINTESIS DEL ANALOGO CICLOPROPANICO DE VALINA

El trabajo describe la preparación de un derivado del aminoácido valina, habiéndose aislado sus dos enantiómeros mediante cromatografía líquida quiral. Este aminoácido no natural puede ser de utilidad para mejorar las propiedades farmacológicas de péptidos con actividad biológica.

*Carlos Cativiela
describe para SIIC los aspectos relevantes de su trabajo
SYNTHESIS AND HPLC ENANTIOSEPARATION OF THE CYCLOPROPANE ANALOGUE OF VALINE (C3VAL)
Institución principal de la investigación
*Universidad de Zaragoza, Zaragoza, España, Zaragoza, España
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Referencias bibliográficas
1. Venkatraman J, Shankaramma SC, Balaram P. Design of folded peptides. Chem Rev 2001; 101:3131-3152.
2. Hruby VJ. Design in topographical space of peptide and peptidomimetic ligands that affect behavior. A chemist's glimpse at the mind-body problem. Acc Chem Res 2001; 34:389-397.
3. Kaul R, Balaram P. Stereochemical control of peptide folding. Bioorg Med Chem 1999; 7:105-117.
4. Salaün J. Cyclopropane derivatives and their diverse biological activities. Top Curr Chem 2000; 207:1-67.
5. Stammer CH. Cyclopropane amino acids (2,3- and 3,4-methanoamino acids). Tetrahedron 1990; 46:2231-2254.
6. Alami A, Calmes M, Daunis J, Jacquier R. Les acides 1-aminocyclopropanecarboxyliques. Propriétés et synthèses. Bull Soc Chim Fr 1993; 130:5-24.
7. Burgess K, Ho KK, Moye-Sherman D. Asymmetric syntheses of 2,3-methanoamino acids. Synlett 1994; 575-583.
8. Jiménez AI, Marraud M, Cativiela C. Cyclopropane analogue of valine: influence of side chain orientation on peptide folding. Tetrahedron Lett 2003; 44:3147-3150.
9. Peggion C, Formaggio F, Crisma M, Toniolo C, Jiménez AI, Cativiela C, Kaptein B, Broxterman QB, Saviano M, Benedetti E. Folding of peptides characterized by c3Val, a highly constrained analogue of valine. Biopolymers 2003; 68:178-191.
10. Oliveros L, López P, Minguillón C, Franco P. Chiral chromatographic discrimination ability of a cellulose 3,5-dimethylphenylcarbamate/10-undecenoate mixed derivative fixed on several chromatographic matrices. J Liq Chromatogr 1995; 18:1521-1532.
11. Minguillón C, Franco P, Oliveros L, López P. Bonded cellulose-derived high-performance liquid chromatography chiral stationary phases. I. Influence of the degree of fixation on selectivity. J Chromatogr A 1996; 728:407-414.
12. Okamoto Y, Yashima E. Polysaccharide derivatives for chromatographic separation of enantiomers. Angew Chem Int Ed 1998; 37:1020-1043.
13. Allenmark SG. Chromatographic enantioseparation: methods and applications. New York: Prentice Hall; 1991. 282 p.
14. Francotte ER. Chromatography as a separation tool for the preparative resolution of racemic compounds. In: Ahuja S, editor. Chiral separations. Applications and technology. Washington DC: American Chemical Society 1997; pp 271–307.
15. Alías M, Cativiela C, Jiménez AI, López P, Oliveros L, Marraud M. Preparative HPLC resolution of the cis cyclohexane analogs of phenylalanine. Chirality 2001; 13:48–55.

Otros artículos de Carlos Cativiela

Cativiela C, Díaz de Villegas MD. Stereoselective synthesis of quaternary alfa-amino acids. Part 1: Acyclic compounds. Tetrahedron: Asymmetry 1998; 9:3517-3599.

Cativiela C, Díaz de Villegas MD. Stereoselective synthesis of quaternary alfa-amino acids. Part 2: Cyclic compounds. Tetrahedron: Asymmetry 2000; 11:645-732.

Cativiela C, Díaz de Villegas MD. 5(2H)-oxazolones and 5(4H)-oxazolones. In: Palmer DC, editor. Oxazoles: synthesis, reactions and spectroscopy; Part B. The chemistry of heterocyclic compounds (Volume 60). John Wiley & Sons: New York, 2004. p 129-330.

Jiménez AI, Cativiela C, Aubry A, Marraud M. Beta-turn preferences induced by 2,3-methanophenylalanine chirality. J Am Chem Soc 1998; 120:9452-9459.

Jiménez AI, Cativiela C, Gómez Catalán J, Pérez JJ, Aubry A, Paris M, Marraud M. Influence of side-chain restriction and NH...pi interaction on the beta-turn folding modes of dipeptides incorporating phenylalanine cyclohexane derivatives. J Am Chem Soc 2000; 122:5811-5821.

Jiménez AI, Cativiela C, Marraud M. A gamma-turn induced by a highly constrained cyclopropane analogue of phenylalanine (c3diPhe) in the solid state. Tetrahedron Lett 2000; 41:5353-5356.

Gil AM, Buñuel E, Jiménez AI, Cativiela C. Stabilisation of the type I beta-turn conformation by a bicyclic analogue of proline. Tetrahedron Lett 2003; 44:5999-6002.

Royo S, De Borggraeve WM, Peggion C, Formaggio F, Crisma M, Jiménez AI, Cativiela C, Toniolo C. Turn and helical peptide handedness governed exclusively by side-chain chiral centers. J Am Chem Soc 2005; 127:2036-2037.

Jiménez AI, Ballano G, Cativiela C. First observation of two consecutive gamma-turns in a crystalline linear dipeptide. Angew Chem Int Ed 2005; 44:396-399.

Para comunicarse con Carlos Cativiela mencionar a SIIC como referencia:
cativiela@unizar.es

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Acerca del trabajo completo

SINTESIS DEL ANALOGO CICLOPROPANICO DE VALINA

Título original en castellano
SINTESIS Y SEPARACION DE ENANTIOMEROS POR HPLC DEL ANALOGO CICLOPROPANICO DE VALINA (C3VAL)

Autor
Carlos Cativiela¹, Ana I. Jiménez², Pilar López³
1 Químico, Universidad de Zaragoza, Catedrático
2 Químico, Consejo Superior de Investigaciones Científicas, Científico Titular
3 Químico, Universidad de Zaragoza, Profesor Titular

Acceso a la fuente original
Chirality
http://www3.interscience.wiley.com/cgi-bin/jhome/37532

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