Thioamide synthesis: Thioacyl-N-phthalimides as thioacylating agents

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3808-3809

  Brain, Christopher T ^a   Hallett, Allan ^a   Ko, Soo Y ^a,b  

^a Novatis Inst for Medical Sciences   (United Kingdom)

^b Samsung Advanced Institute of Technology (SAIT)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

PHTHALIMIDE DERIVATIVE; THIOAMIDE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 0030851935     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970528v     Document Type: Article

References (24)

1. Review: Spatola, A. F. In Chemistry and Biochemistry of Amino Acids, Peptides and Proteins; Weinstein, B., Ed.; Marcel Dekker: New York, 1983; Vol. 7, Chapter 5, pp 267-357.
2. Synthesis of a more complex multithiopeptide incorporating n adjacent thioamide linkages would require thionation of a preformed peptide of (n + 1) residues.
3. (a) Clausen, K.; Thorsen, M.; Lawesson, S.-O.; Spatola, A. F. J. Chem. Soc., Perkin Trans. 1 1984, 785-798.
4. (b) Thorsen, M.; Yde, B.; Pedersen, U.; Clausen, K.; Lawesson, S.-O. Tetrahedron 1983, 39, 3429-3435.
5. Direct thionation of a peptide usually leads to a mixture of regioisomeric thiopeptides unless a strong steric/conformational bias is present; for example, see: Seebach, D.; Ko, S. Y.; Kessler, H.; Köck, M.; Reggelin, M.; Schmieder, P.; Walkinshaw, M. D.; Bölsterli, J. J.; Bevec, D. Helv. Chim. Acta 1991, 74, 1953-1990.
6. Unverzagt, C.; Geyer, A.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1992, 31, 1229-1230.
7. This aspect will be discussed fully in a later publication.
8. (a) Zacharie, B.; Sauvé, G.; Penney, C. Tetrahedron 1993, 49, 10489-10500.
9. (b) Belleau, B.; Brillon, D.; Sauvé, G.; Zacharie, B. U.S. Patent No. 5,138,061, Aug 11, 1992.
10. (c) Reported during the preparation of this paper: Shalaby, M. A.; Grote, C. W.; Rapoport, H. J. Org. Chem. 1996, 61, 9045-9048.
11. (a) Høeg-Jensen, T.; Olsen, C. E.; Holm, A. J. Org. Chem. 1994, 59, 1257-1263.
12. (b) Katritzky, A. R.; Moutou, J.-L.; Yang, Z. Synthesis 1995, 1497-1505.
13. (c) Katritzky, A. R.; Moutou, J.-L.; Yang, Z. Synlett 1995, 99-100.
14. (d) Le, H.-T.; Mayer, M.; Thoret, S.; Michelot, R. Int. J. Peptide Protein Res. 1995, 45, 138-144.
15. (e) DeBruin, K. E.; Boros, E. E. J. Org. Chem. 1990, 55, 6091-6098.
16. (f) Elmore, D. T.; Guthrie, D. J. S.; Kay, G.; Williams, C. H. J. Chem. Soc., Perkin Trans. 1 1988, 1051-1055.
17. For a review of Lawesson's reagent see: Cava, M. P.; Levinson, M. I. Tetrahedron 1985, 41, 5061-5087.
18. A literature survey revealed the following references to (thioacyl)-N-phthalimides: (a) Goerdeler, J.; Stadelbauer, K. Chem. Ber. 1965, 98, 1556-1561. (b) Goerdeler, J.; Horstmenn, H. Chem. Ber. 1960, 93, 670-678; 1960, 93, 663-670.
19. A literature survey revealed the following references to (thioacyl)-N-phthalimides: (a) Goerdeler, J.; Stadelbauer, K. Chem. Ber. 1965, 98, 1556-1561. (b) Goerdeler, J.; Horstmenn, H. Chem. Ber. 1960, 93, 670-678; 1960, 93, 663-670.
20. A literature survey revealed the following references to (thioacyl)-N-phthalimides: (a) Goerdeler, J.; Stadelbauer, K. Chem. Ber. 1965, 98, 1556-1561. (b) Goerdeler, J.; Horstmenn, H. Chem. Ber. 1960, 93, 670-678; 1960, 93, 663-670.
21. Unless indicated otherwise, amino acid symbols represent the L-enantiomers.
22. (a) The phthalimide ring is completely planar, while the thioacyl group lies ca. 36° out of the plane and, therefore, is not stabilized by conjugation.
23. (b) The authors have deposited atomic coordinates for compounds 3a and 3b with the Cambridge Crystallographic Data Centre. The coordinates may be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
24. Diastereoisomeric purity of the coupling product of 3e and D-alanine benzylamide: 98.9%. See also reaction of 3e with L-alanine benzylamide (Table 1).