Solid-phase synthesis and utilization of side-chain reactive unnatural amino acids

Tetrahedron Letters

Volumn 44, Issue 46, 2003, Pages 8403-8406

  O'Donnell, Martin J ^a   Alsina, Jordi ^a   Scott, William L ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

Alkylation; Combinatorial chemistry; Nucleophilic substitution; Proline homologs; Schiff base activation; Side chain diversity; Spirocyclic amino acids; , dihaloalkanes

Indexed keywords

ALKANE DERIVATIVE; AMINO ACID; BENZOPHENONE DERIVATIVE; BROMINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CHLORIDE; GLYCINE; IMINE; NITRILE; PROLINE; RESIN; SULFIDE;

ALKYLATION; ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID; SYNTHESIS;

EID: 0141956507     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.119     Document Type: Article

References (14)

1. For lead references, see: Asymmetric Synthesis of Novel Sterically Constrained Amino Acids; Symposium-in-Print, Hruby, V. J.; Soloshonok, V. A., Eds. Tetrahedron 2001, 57, 6329-6650.
2. Scott W.L., O'Donnell M.J., Delgado F., Alsina J. J. Org. Chem. 67:2002;2960-2969.
3. Scott W.L., Alsina J., O'Donnell M.J. J. Comb. Chem. 5:2003;684-692.
4. For selected reports of solution-phase synthesis and use of ω-halo-α-amino acid derivatives, see footnote 11 in Ref. 2.
5. For recent reviews concerning the solution-phase synthesis of cyclic amino acid derivatives, see: (a) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645-732. (b) Park, K.-H.; Kurth, M. J. Tetrahedron 2002, 58, 8629-8659.
6. For recent reviews concerning the solution-phase synthesis of cyclic amino acid derivatives, see: (a) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645-732. (b) Park, K.-H.; Kurth, M. J. Tetrahedron 2002, 58, 8629-8659.
7. For examples of applications of organic-soluble, nonionic phosphazine bases BEMP and BTPP from earlier studies, see Refs. 2 and 3.
8. For reports on the solid-phase synthesis of proline derivatives, see footnote 4 in Ref. 3.
9. For the solution-phase synthesis of similar derivatives using this methodology, see: O'Donnell M.J., Bruder W.A., Eckrich T.M., Shullenberger D.F., Staten G.S. Synthesis. 1984;127-128.
10. For the solid-phase preparation of analogs of 10c under similar conditions, see: Bhandari A., Jones D.G., Schullek J.R., Vo K., Schunk C.A., Tamanaha L.L., Chen D., Yuan Z., Needels M.C., Gallop M.A. Bioorg. Med. Chem. Lett. 8:1998;2303-2308.
11. Colman R.F. Creighton T.E. Protein Function. 2nd Ed. 1997;155-183 IRL Press, Oxford, UK.
12. McNamara L.M.A., Andrews M.J.I., Mitzel F., Siligardi G., Tabor A.B. J. Org. Chem. 66:2001;4585-4594.
13. Blackwell H.E., Sadowsky J.D., Howard R.J., Sampson J.N., Chao J.A., Steinmetz W.E., O'Leary D.J., Grubbs R.H. J. Org. Chem. 66:2001;5291-5302.
14. Equipment and general procedures for parallel manual solid-phase organic synthesis are described in Refs. 2 and 3.