Stereospecific synthesis of 4-carboxyphenylalanine and derivatives for use in Fmoc-based solid-phase peptide synthesis

Tetrahedron Letters

Volumn 37, Issue 37, 1996, Pages 6661-6664

  Wang, Wei ^a   Obeyesekere, Nihal U ^a   McMurray, John S ^a  

^a UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOTENSIN II DERIVATIVE;

ARTICLE; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDE SYNTHESIS; TECHNIQUE;

EID: 0030576953     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)01490-6     Document Type: Article

References (21)

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2. 2. Franz, R.G.; Weinstock, J.; Calvo, R.R.; Saraanen, J.; Aiyar, N. Org. Prep. Proc., Int 1994, 26, 533-538.
3. 3. (a) Tilley, J.W.; Danho, W.; Lovey, K.; Wagner, R.; Swistok, J.; Makofske, R.; Michalewsky, J.; Triscari, J.; Nelson, D.; Weatherford, S. J. Med. Chem. 1991, 34, 1125-1136.
4. (b) Tilley, J.W.; Sarabu, R.; Wagner, R.; Mulkerins, K. J. Org. Chem. 1990, 55, 906-910.
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6. 5. Wrobel, J.; Dietrich, A. Tetrahedron Letters 1993, 34, 3543-3546.
7. 6. Nowak, M.W.; Kearney, P.C.; Sampson, J.R.; Saks, M.E.; Labarca, C.G.; Silverman, S.K.; Zhong, W.; Thorson, J.; Abelson, J.N.; Davidson, N.; Schultz, P.G.; Dougherty, D.A.; Lester, H.A. Science 1995, 268, 439-442.
8. 7. (a) Cacchi, S.; Ciattini, P.G.; Morera, E.; Ortat, G. Tetrahedron Letters 1986, 27, 3931-3934;
9. (b) Cacchi, S.; Lupi, A. Tetrahedron Letters 1992, 33, 3939-3942.
10. 8. (a) Atherton, E.; Sheppard, R.C. Solid Phase Peptide Synthesis A Practical Approach; IRL Press: Oxford, 1989.
11. (b) Fields, G.B.; Noble, R.L. Int. J. Peptide Protein Res. 1990, 35, 161-214.
12. 3 in water and acetone at r.t. for 2 h to afford 0.58 gm (1.15 mmol) of the L enantiomer of Fmoc-p-Cpa(O-t-Bu)-OH, 5. The yield of the last two steps was 90% and the overall yield from 1 was 46%.
13. 5]AT II, calculated, 1060.2; found, 1060.7
14. 11. Bodanszky, M.; Bodanszky, A. The Practice of Peptide Synthesis; Springer-Verlag: Berlin, 1984; pp 37-38.
15. 12. Harnisch, W.; Morera, E.; Ortar, G. J. Org. Chem. 1985, 50, 1990-1992.
16. 13. Armstrong, A.; Brackenridge, I.; Jackson, R.F.W.; Kirk, J.M. Tetrahedron Letters 1988, 29, 2483-2486.
17. 14. Fmoc-D,L-4-Cpa(O-t-Bu)-OH was synthesized by (1) alkylation of N-diphenylmethylene glycine methyl ester (O'Donnel, M.J.; Polt, R.L. J. Org. Chem. 1982, 47, 2663-2666) with tert-butyl α-bromo-paratoluate (ref 15) in the presence of potassium tert-butoxide, (2) acidolytic removal of the diphenylmethylene protecting group, (3) saponification of the methyl ester, and (4) amino protection with Fmoc-OSu.
18. 15. Prepared by treatment of para-toluyl chloride with potassium tert-butoxide followed by bromination with NBS.
19. 16. (a) Kanda, P.; Kennedy, R.C.; Sparrow, J.T. Int. J. Peptide Protein. Res. 1991, 38, 385-391;
20. (b) Sparrow, L.T.; Knieb-Cordonier, N.G.; Kanda, P.; Obeyesekere, N.U.; McMurray, J.S. Peptides 1994. Proc 23rd European Peptide Symp.; Maia, H.L.S. Ed.; ESCOM: Leiden; 1995; pp. 281-282.
21. 17. Analytical HPLC was carried out on a Hewlett-Packard 1090 liquid chromatograph using a 2.1 × 25 mm Phenomenex C18 column. The gradient was 10-50% MeCN/30 min with a flow rate of 0.7 mL/min. Elution was monitored with a diode array detector at both 230 nm and 274 nm.