Synthesis of highly fluorinated dipeptide building blocks

Tetrahedron Letters

Volumn 41, Issue 20, 2000, Pages 3825-3828

  Koksch, Beate ^a   Mütze, Kerstin ^a   Osipov, Sergej N ^b   Golubev, Alexander S ^b   Burger, Klaus ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

trifluoromethyl amino acid; 4+1 cycloaddition; Isocyanides; N acylimines

Indexed keywords

ALPHA AMINO ACID; DIPEPTIDE; HEXAFLUOROACETONE; IMINE; PYRUVIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; FLUORINATION; HYDROLYSIS; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; REACTION ANALYSIS;

EID: 0342748743     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00540-2     Document Type: Article

References (19)

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2. (b) Marshal, G. R.; Clarc, J. D.; Dunbar Jr., J. B.; Smith, G. D.; Zabrocki, J.; Redlinski, A. S.; Leplawy, M. T. Int. J. Pept. Protein Res. 1998, 32, 544.
3. (a) Sewald, N.; Burger, K. Synthesis of β-Fluorine Containing Amino Acids; In Fluorine Containing Amino Acids - Synthesis and Properties; Kukhar′, V. P.; Soloshonok, V. A., Eds.; J. Wiley & Sons: Chichester, New York, Brisbane, Toronto, Singapore, 1995; pp. 139-220.
4. (b) Koksch, B.; Sewald, N.; Jakubke, H.-D.; Burger, K. Synthesis and Incorporation of α-Trifluoromethyl Substituted Amino Acids into Peptides. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. P.; Welch, J. T., Eds.; ACS Symposium Series 639: Washington DC, 1996; 42, and references cited therein.
5. (c) Koksch, B.; Sewald, N.; Hofmann, H.-J.; Burger, K.; Jakubke, H.-D. J. Pept. Science 1997, 3, 157.
6. Kobsev, S. P.; Soloshonok, V. A.; Yagupol'skii, Yu. L.; Kukhar', V. P. J. Gen. Chem. USSR 1989, 59, 801.
7. (a) Schierlinger, Ch.; Burger. K. Tetrahedron Lett. 1992, 33, 193.
8. (b) Burger, K.; Mütze, K.; Hollweck, W.; Koksch, B.; Kuhl, P.; Jakubke, H.-D.; Riede, J.; Schier, A. J. prakt. Chem. 1993, 335, 321.
9. (a) Sewald, N.; Hollweck, W.; Mütze, K.; Schierlinger, Ch.; Seymour, L. C.; Gaa, K.; Burger, K.; Koksch, B.; Jakubke, H.-D. Amino Acids 1995, 8, 197.
10. (b) Hollweck, W.; Burger, K. J. prakt. Chem. 1995, 337, 391.
11. (c) Hollweck, W.; Sewald, N.; Michel, T.; Burger, K. Liebigs Ann. Chem. 1997, 2549.
12. Osipov, S. N.; Sewald, N.; Kolomiets, A. F.; Fokin, A. V.; Burger, K. Tetrahedron Lett. 1996, 615.
13. The only example of this strategy so far described: Weygand, F.; Steglich, W.; Oettmeier, W.; Maierhofer, A.; Loy, R. S. Angew. Chem. 1966, 78, 640; Angew. Chem., Int. Ed. Engl. 1966, 5, 600.
14. The only example of this strategy so far described: Weygand, F.; Steglich, W.; Oettmeier, W.; Maierhofer, A.; Loy, R. S. Angew. Chem. 1966, 78, 640; Angew. Chem., Int. Ed. Engl. 1966, 5, 600.
15. (a) Zeifman, Yu. V.; Gambaryan, N. P.; Knunyants, I. L. Izvest. Acad. Nauk SSSR, Ser. Khim. 1965, 2046.
16. (b) Steglich, W.; Burger, K.; Dürr, W.; Burgis, E. Chem. Ber. 1974, 107, 1488.
17. (c) Burger, K.; Gaa, K. Chem.-Ztg. 1990, 114, 101.
18. Burger, K.; Schierlinger, Ch.; Mütze, K. J. Fluorine Chem. 1993, 65, 149.
19. 4 (510.33): calcd C 44.71, H 3.75, N 5.49%; found: C 45.11, H 3.72, N 5.63%.