Solid-phase synthesis of modified oligopeptides via Passerini multicomponent reaction

Tetrahedron Letters

Volumn 44, Issue 11, 2003, Pages 2367-2370

  Basso, Andrea ^a   Banfi, Luca ^a   Riva, Renata ^a   Piaggio, Paolo ^a   Guanti, Giuseppe ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

IBX; Multicomponent Passerini reaction; Photoacoustic IR spectroscopy; Protease inhibitors; Solid supported isocyanides

Indexed keywords

AMINOALDEHYDE; CARBOXYLIC ACID DERIVATIVE; OLIGOPEPTIDE;

ARTICLE; CHEMICAL REACTION; DEPROTECTION REACTION; INFRARED SPECTROSCOPY; MIGRATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PASSERINI MULTICOMPONENT REACTION; PHOTOACOUSTIC SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; RELIABILITY; SOLID; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0037430642     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00238-7     Document Type: Article

References (16)

1. Ugi I., Heck S. Comb. Chem. HTS. 4:2001;1-34.
2. Banfi L., Guanti G., Riva R. Chem. Commun. 2000;985-986.
3. Otto H.-H., Schirmeister T. Chem. Rev. 97:1997;133-171.
4. Banfi L., Guanti G., Riva R., Basso A., Calcagno E. Tetrahedron Lett. 43:2002;4067-4069.
5. Owens T.D., Semple J.E. Org. Lett. 3:2001;3301-3304.
6. Owens T.D., Araldi G.-L., Nutt R.F., Semple J.E. Tetrahedron Lett. 42:2001;6271-6274.
7. Tadesse, S.; Balan, C.; Jones, W.; Viswanadhan, V.; Hulme, C.; 223rd ACS National Meeting, 2002, Orlando, FL, USA.
8. Huber, V. J.; Nagula, G.; Lum, C.; Goodman, B. A. Abstracts of Papers of the American Chemical Society 2001, 221, 140-ORGN.
9. Yan B., Gremlich H.U., Moss S., Coppola G.M., Sun Q., Liu L. J. Comb. Chem. 1:1999;46-54.
10. Gosselin F., Di Renzo M., Ellis T.H., Lubell W.D. J. Org. Chem. 61:1996;7980-7981.
11. Rasoul F., Ercole F., Pham Y., Bui C.T., Wu Z.M., James S.N., Trainor R.W., Wickham G., Maeji N.J. Biopolymers. 55:2000;207-216.
12. Atrash B., Bradley M., Kobylecki R., Cowell D., Reader J. Angew. Chem., Int. Ed. Engl. 40:2001;938-941.
13. 6) mixture of two diastereoisomers: 33.8, 34.2 and 34.4, 36.8, 42.1, 53.2, 71.2 and 73.3, 126.0, 126.1, 126.6, 127.9, 128.0, 128.1, 128.7, 128.9, 129.0, 129.2, 136.4 and 136.5, 136.8 and 139.1, 169.6 and 169.7, 171.6 and 171.8, 173.2.
14. Unpublished results.
15. Pearson W.H., Clark R.B. Tetrahedron Lett. 38:1997;7669-7672.
16. 6): 197.0, 172.5, 169.9, 160.4, 136.0, 128.9, 128.1, 126.2, 49.3, 41.3, 34.7, 33.0, 15.5.