Solid phase synthesis of peptides containing novel L-phenylalanine derivatives substituted with vicinal tricarbonyl moieties

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8479-8482

  Fretz, Heinz ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

PHENYLALANINE DERIVATIVE;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS; REACTION ANALYSIS;

EID: 0030592764     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01979-X     Document Type: Article

References (11)

1. 1. Fretz, H. Tetrahedron Lett. 1996, foregoing paper.
2. 2. Rink, H. Tetrahedron Lett. 1987, 28, 3787.
3. 3. Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. Tetrahedron Lett. 1989, 30, 1927.
4. 4. Kaiser, E. T.; Colescott, R.L.; Bossinger, C. D.; Cock, P. I. Anal. Biochem. 1970, 54, 595.
5. 5. Wade, J. D.; Bedford, J.; Sheppard, R. C., Tregaer, G. W. Peptide Research 1991, 4 (3), 194.
6. 2O/ 0.1% TFA (eluent A) and acetonitrile/ 0.09% TFA (eluent B) from 2% to 100% B over 10 min; flow rate 1.5 ml/min, detection at 215 nm.
7. 18-derivatized silicagel, Merck, Darmstadt, FRG; column length 46 cm, diameter 3.6 cm; flow rate 60 ml/min; detection at 215nm), eluted with an acetonitrile-water gradient containing 0.1% of TFA.
8. 9P: 561.59 Da; for the hydrate: 579.60 Da).
9. 2O (v/v) gave a compound that was shown to be identical with peptide 3a (HPLC, MS).
10. 10. The rearrangement and cleavage of α,β-dioxopropionic acid derivatives under alcaline conditions was investigated earlier: Rodé-Gowal, H.; Dao, H. L.; Dahn, H. Helv. Chim. Acta 1974, 57, 240. For the decarboxylation under acidic conditions we propose the following mechanism: (formula presented) The proposed mechanism is consistent with the product isolated.
11. 11. Wasserman, H. H.; Baldino, C. M.; Coats, S. J. J. Org. Chem. 1995, 60, 8231 and references cited therein.