Solid phase hydantoin synthesis: An efficient and direct conversion of Fmoc-protected dipeptides to hydantoins

Tetrahedron Letters

Volumn 40, Issue 13, 1999, Pages 2493-2496

  Chong, Pek Y ^a   Petillo, Peter A ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBAMIC ACID; DIPEPTIDE; HYDANTOIN; ISOCYANATE; PHOSGENE; RESIN;

ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTEIN CONFORMATION; SOLID STATE; SYNTHESIS;

EID: 0033605929     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00243-9     Document Type: Article

References (9)

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2. (b) Thompson, L. A.; Ellman, J. A.; Chem. Rev. 1996, 96, 555 and references cited therein.
3. DeWitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Cody, D. M. R.; Pavia, M. R. Proc. Natl. Acad. Sci. USA. 1993, 90, 6909-6913.
4. Dressman, B. A.; Spangle, L. A.; Kaldor, S. W. Tetrahedron Lett. 1996, 37, 937-940.
5. Xiao, X.; Ngu, K.; Chao, C.; Patel, D. J. Org. Chem. 1997, 62, 6968-6973.
6. Nefzi, A.; Ostresh, J. M.; Giulianotti, M.; Houghten, R. A. Tetrahedron Lett. 1998, 38, 8199-8202.
7. Chong, P. Y.; Janicki, S. J.; Petillo, P. A. J. Org. Chem. 1998, 63, 8515-8521.
8. X = 1917.2 Hz), 3.95 (ddd, 1H, J = 9.4, 4.4, 1.0 Hz), 3.29 (ABX, see above), 1.57 (dseptd, J = 9.5, 6.6, 4.4 Hz), 1.17 (ddd, 1H, J = 13.7, 9.4, 4.4 Hz), 0.94 (ddd, 1H, J = 13.7, 9.5, 4.4 Hz), 0.78 (d, 6H, J = 6.6 Hz).
9. 18 3μm column (50 × 4.6 mm); the purity was estimated on analytical traces at λ = 214 nm.