Applications of the mitsunobu reaction in peptide chemistry

Journal of Peptide Science

Volumn 4, Issue 1, 1998, Pages 1-14

  Wiśniewski, Kazimierz ^a   Kołdziejczyk, Aleksandra S ^a   Falkiewicz, Bogdan ^a  

^a UNIVERSITY OF GDA SK   (Poland)

Author keywords

Amino acid derivatives synthesis; Mitsunobu reaction; N alkyl amino acid synthesis; Peptide oxazolines and thiazolines; lactam formation

Indexed keywords

AMINO ACID; LACTONE; PEPTIDE;

CHEMISTRY; ESTERIFICATION; REVIEW; SYNTHESIS;

AMINO ACIDS; ESTERIFICATION; LACTONES; PEPTIDES;

EID: 0031989415     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1387(199802)4:1<1::AID-PSC132>3.0.CO;2-R     Document Type: Review

References (59)

1. O. Mitsunobu (1981). The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis, 1-28.
2. D. L. Hughes (1992). The Mitsunobu reaction. Org. Reactions 42, 337-656.
3. D. L. Hughes (1996). Progress in the Mitsunobu reaction. Org. Prep. Proced. Int. 28, 127-164.
4. E. Fabiano, B. T. Golding and M. M. Sadeghi (1987). A simple conversion of alcohols into amines. Synthesis, 190-192.
5. J. March: Advanced Organic Chemistry. Reactions, Mechanisms and Structure. p. 1220, John Wiley, New York 1992.
6. M. C. Viaud and P. Rollin (1990). Zinc azide and Mitsunobu substitution. An expedient method for the one-pot azidation of alcohols. Synthesis, 130-132.
7. O. Mitsunobu, M. Wada and T. Sano (1972). Stereospecific and stereoselective reactions. I. Preparation of amines from alcohols. J. Am. Chem. Soc. 94, 679-680.
8. M. Wada, T. Sano and O. Mitsunobu (1973). Stereospecific and stereoselective reactions. II. Preparation of esters of N-phthaloyl-α-amino acids from esters of α-hydroxy acid. Bull. Chem. Soc. Jpn. 46, 2833-2835.
9. 15N-labeling. J. Chem. Soc. Perkin Trans. 1, 245-253.
10. L. Gehn and U. Ragnarsson (1988). Synthesis and use of benzyl tert-butyl iminocarbonate, a versatile reagent for the preparation of amines. Collect. Czech. Chem. Commun. 53, 2778-2786.
11. U. Schmidt, K. Mundinger, B. Riedl, G. Haas and R. Lau (1992). Synthesis of enantiomerically pure and compatibly protected (2S, 3r)- and (2S, 3S)-diaminobutyric acids. Synthesis, 1201-1202.
12. K. Mundinger, PhD Thesis, University of Stuttgart 1991.
13. J. A. Campbell and D. J. Hart (1993). Tert-butyl[[2-(trimethylsilyl)ethyl]sulphonyl]carbamate: A new reagent for use in Mitsunobu reactions. J. Org. Chem. 58, 2900-2903.
14. N2′-dichotomy of the Mitsunobu amination of allylic alcohols. Synthesis, 101-112.
15. T. Kolasa and M. J. Miller (1987). Reactions of α-hydroxy carbonyl compounds with azodicarboxylates and triphenylphosphine: Synthesis of α-N-hydroxy amino acid derivatives. J. Org. Chem. 52, 4978-4984.
16. 6-hydroxylysine. J. Am. Chem. Soc. 104, 3096-3101.
17. D. Papaioannou, C. Athanassopoulos, V. Magafa, N. Karamanos, G. Stavropoulos, A. Napoli, G. Sindona, D. W. Aksnes and G. W. Francis (1994). Redox N-alkylation of tosyl protected amino acid and peptide esters. Acta. Chem. Scand. 48, 324-333.
18. J. R. Henry, L. R. Marcin, M. H. McIntosh, P. M. Scola, G. D. Harris Jr and S. M. Weinreb (1989). Mitsunobu reactions of N-alkyl and N-acyl sulphonamides - an efficient route to protected amines. Tetrahedron Lett. 30, 5709-5712.
19. K. Wiśniewski and A. S. Kołodziejczyk (1997). Pmc-protected amino acid esters as substrates in N-alkylamino acid synthesis. Tetrahedron Lett. 38, 483-486.
20. G-2,2,5,7,8-pentamethylchroman-6-sulphonyl-L-arginine: A new acid labile derivative for peptide synthesis. Tetrahedron Lett. 28, 2287-2290.
21. B. Falkiewicz, L. Łankiewicz, B. Liberek and K. Wiśniewski (1997). A new synthesis of PNA monomers under mild conditions. Peptides 1996. Proceedings of the 24th Symposium of EPS (in press).
22. 4 analogs: Synthesis and implications for the CCK-B receptor-bound conformation. J. Med. Chem. 38, 137-149.
23. G. Ceulemans, K. Khan, A. Van-Schepdael and P. Herdewijn (1995). Peptide analogues of DNA consisting of L-alpha-amino-gamma-thymine butyric acid and L-valine subunits. Nucleosides Nucleotides 14, 813-816.
24. H. Wojciechowska, R. Pawlowicz, R. Andruszkievicz and J. Grzybowska (1978). Conversion of protected serine and threonine to corresponding dehydroamino acids under mild conditions. Tetrahedron Lett. 42, 4063-4064.
25. 5-hydroxy-L-ornithine. J. Med. Chem. 34, 956-968.
26. W. P. Malachowski and J. K Coward (1994). The chemistry of phosphapeptides: Formation of functionalised phosphonochloridates under mild conditions and their reaction with alcohols and amines. J. Org. Chem. 59, 7616-7624.
27. W. P. Malachowski and J. K Coward (1994). The chemistry of phosphapeptides: Investigations on the synthesis of phosphonamidate, phosphonate, and phosphinate analogues of glutamyl-γ-glutamate. J. Org. Chem. 59, 7625-7634.
28. A. Golubev, N. Sewald and K. Burger (1995). An efficient approach to the family of 4-substituted pipecolic acids. Syntheses of 4-oxo-, cis-4-hydroxy-, and trans-4-hydroxy-L-pipecolic acids from L-aspartic acid. Tetrahedron Lett. 36, 2037-2040.
29. E. Grochowski and J. Jurczak (1977). A new method for the preparation of N-acyloxyphthalimides and N-acyloxysuccinimides. Synthesis, 277-279.
30. G. Emmer, M. A. Grassberger, J. G. Meingassner, G. Schultz and M. Schaude (1994). Derivatives of a novel cyclopeptolide. 1. Synthesis, antifungal activity, and structure-activity relationships. J. Med. Chem. 37, 1908-1917.
31. T. Imaeda, Y. Hamada and T. Shioiri (1994). Efficient syntheses of geodiamolide A and jaspamide, cytotoxic and antifungal cyclic depsipeptides of marine sponge origin. Tetrahedron Lett. 35, 591-594.
32. B. M. Degnan, C. J. Hawkins, M. F. Lawin, E. J. McCaffrey, D. L. Parry, A. L. van den Brenk and D. J. Waters (1989). New cyclic peptides with cytotoxic activity from the Ascidian Lissoclinum Patella. J. Med. Chem. 32, 1349-1354, and references cited therein.
33. P. Wipf and C. P. Miller (1992). Total synthesis of westiellamide. J. Am. Chem. Soc. 114, 10975-10977.
34. A. J. Robichaud and A. I. Meyers (1991). Asymmetric additions to chiral naphtyloxazolines. An entry into tetracyclic terpene ring systems related to aphidicolin, scopadulcic acid, and kauranes. J. Org. Chem. 56, 2607-2609.
35. D. M. Roush and M. M. Patel (1985). A mild procedure for the preparation of 2-oxazolines. Synth. Commun. 15, 675-679.
36. N. Galeotti, C. Montagne, J. Poncet and P. Jouin (1992). Formation of oxazolines and thiazolines in peptides by the Mitsunobu reaction. Tetrahedron Lett. 33, 2807-2810.
37. P. Wipf and C. P. Miller (1992). A short, stereospecific synthesis of dihydrooxazoles from serine and threonine derivatives. Tetrahedron Lett. 33, 907-910.
38. P. Wipf and C. P. Miller (1992). An investigation of the Mitsunobu reaction in the preparation of peptide oxazolines, thiazolines and aziridines. Tetrahedron Lett. 33, 6267-6270.
39. P. Wipf and P. C. Fritch (1994). Synthesis of peptide thiazolines from β-hydroxythioamides. An investigation of racemization in cyclodehydration protocols. Tetrahedron Lett. 35, 5397-5400.
40. P. G. Mattingly, J. F. Kerwin Jr and M. J. Miller (1979). A facile synthesis of substituted N-hydroxy-2-azetidinones. A biogenic type β-lactam synthesis. J. Am. Chem. Soc. 101, 3983-3985.
41. M. J. Miller, P. G. Mattingly, M. A. Morrison and J. F. Kerwin Jr (1980). Synthesis of β-lactams from substituted hydroxamic acids. J. Am. Chem. Soc. 102, 7026-7032.
42. G. M. Salituro and C. A. Townsend (1990). Total synthesis of (-)-nocardicins A-G: A biogenetic approach. J. Am. Chem. Soc. 112, 760-770.
43. R. B. Sykes, C. M. Cimarusti, D. P. Bonner, K. Bush, D. M. Floyd, N. H. Georgopapadakou, W. M. Koster, W. C. Liu, W. L. Parker, P. A. Principe, M. L Rathnum, W. A. Slusarchyk, W. H. Trejo and J. S. Wells (1981). Monocyclic beta-lactam antibiotics produced by bacteria. Nature 291, 489-491.
44. D. M. Floyd, A. W. Fritz, J. Plusec, E. R. Weaver and C. M. Cimarusti (1982). Monobactams. Preparation of (S)-3-amino-2-oxoazetidine-1-sulfonic acids from L-α-amino-β-hydroxy acids via their hydroaxamic esters. J. Org. Chem. 47, 5160-5167.
45. A. K. Bose, D. P. Sahu and M. S. Manhas (1981). Stereoselective chiral synthesis of N-aryl-α-amino-β-lactams from β-hydroxy-α-amino acids. J. Org. Chem. 46, 1229-1230.
46. A. K. Bose, M. A. Manhas, D. P. Sahu and V. R. Hedge (1984). Stereospecific cyclizatlon of β-hydroxy aryl amides to β-lactams. Can. J. Chem. 62, 2498-2505.
47. M. J. Miller and P. G. Mattingly (1983). The direct chemical conversion of peptides to β-lactams. Tetrahedron 15, 2563-2570.
48. F. Farouz-Grant and M. J. Miller (1993). Synthesis of novel 1-aminocyclopropane-1-carboxylic acid (ACC)-containing β-lactams. Bioorg. Med. Chem. Lett. 3, 2423-2428.
49. J. C. Sheehan and F. J. Guziec (1973). Amino group protection in peptide synthesis. The 4,5-diphenyl-4-oxazolin-2-one group. J. Org. Chem. 38, 3034-3040.
50. H. Umezawa, T. Aoyagi, H. Morishima, M. Matsuzaki and M. Hamada (1970). Pepstatin, a new pepsin inhibitor produced by Actinomycetes. J. Antibiot. 23, 259-262.
51. M. Jones, J. Sueiras-Diaz, M. Szelke, B. Leckie and S. Beattie in: Peptides, Structure and Function. Proceedings of the 9th American Peptide Symposium, C. M. Deber, V. J. Hruby and K. D. Kopple, Eds., p. 759-762, Pierce Chemical Co., Rockford IL 1985.
52. S. Thaisrivongs, H. J. Schostarez, D. T. Pals and S. R. Turner (1987). α,α-Difluoro-β-aminodeoxystatine-containing renin inhibitory peptides. J. Med. Chem. 30, 1837-1842.
53. L. D. Arnold, T. H. Kalantar and J. C. Vederas (1985). Conversion of serine to stereochemically pure β-substituted α-amino acids via β-lactones. J. Am. Chem. Soc. 107, 7105-7109.
54. W. L. Parker, M. L. Rathnum and W. Liu (1982). SQ 26,517 - a β-lactone produced by a Bacillus species. J. Antibiot. 35, 900-902.
55. D. Papaioannou, G. Stavropoulos, K. Karagiannis, G. W. Francis, T. Brekke and D. W. Aksnes (1990). Simple synthesis of cis-4-hydroxy-L-proline and derivatives suitable for use as intermediates in peptide synthesis. Acta. Chem. Scand. 44, 243-251.
56. G. Stavropoulos, K. Karagiannis, D. Vynios, D. Papaioannou, D. W. Aksnes, N. A. Froystein and G. W. Francis (1991). Solid phase synthesis and spectroscopic studies of TRH analogues incorporating cis- and trons-4-hydroxy-L-proline. Acta. Chem. Scand. 45, 1047-1054.
57. 2]TRH and analogues incorporating cis- and trons-4-hydroxy-L-proline. Acta. Chem. Scand. 49, 103-114.
58. P. J. Maurer and M. J. Miller (1983). Total synthesis of a mycobactin: Mycobactin S2. J. Am. Chem. Soc. 105, 240-245.
59. G. A. Snow (1970). Mycobactins: iron-chelating growth factors from mycobacteria. Bacteriol Rev. 34, 99-125.