Effect of scavengers in acidolytic cleavage of Cys(Acm)-containing peptides from solid support: Isolation of an ethanedithiol disulfide adduct

Tetrahedron Letters

Volumn 37, Issue 24, 1996, Pages 4117-4120

  Singh, Prahlad R ^a   Rajopadhye, Milind ^a   Clark, Stephen L ^a   Williams, Neal E ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANISOLE; CYSTEINE; DIMERCAPTOETHANE; DISULFIDE; PHENOL; RADIOPHARMACEUTICAL AGENT; RESIN; SCAVENGER; SILANE DERIVATIVE; TRIPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MASS SPECTROMETRY; OXIDATION; PEPTIDE SYNTHESIS;

EID: 0029992130     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00614-4     Document Type: Article

References (12)

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2. (b) Karlström, A. H.; Undén, A. E. Tetrahedron Lett. 1995, 36, 3909-3912.
3. (a) Gairf, M.; Lloyd-Williams, P.; Albericio, F.; Giralt, E. Tetrahedron Lett. 1994, 35, 175-178.
4. (b) King, D. S.; Fields, C. G.; Fields, G. B. Int. J. pep. Prot. Res. 1990, 36, 255-266.
5. Veber, D. F.; Milkowski, J. D.; Varga, S. L.; Denkewalter, R. G.; Hirschmann, R. J. Am. Chem. Soc. 1972, 94 (15), 5456-5461.
6. (a) Bryson, N.; Lister-James, J.; Jones, A. G.; Davis, W. M.; Davison, A. Inorg. Chem. 1990, 29, 2948-2951.
7. (b) Lister-James, J.; McBride, W. J.; Buttram, S .; Civitello, E. R.; Martel, L. J. ; Pearson, D. A.; Wilson, D. M.; Dean, R. T. In Tc and Re in Chem. and Nuc. Med.; Nicolini, M.; Bandoli, G.; Mazzi, U. Eds.; SGE Ditoriali, Padova, 1995; pp 269-274.
8. Typical procedure used for the cleavage of the peptide from the resin involved incubation of 500 mg of the peptide-resin with 10 ml of the cocktail mixture at room temperature with occasional swirling. After two hours the resin was filtered and washed with TFA (2×4 ml). The filtrate was then concentrated to ∼ 1-2 ml in vacuo and triturated with cold diethyl ether (10 ml). The product was filtered, washed with cold ether (2×8 ml) and dried overnight before analysis.
9. Novabiochem catalogue 1994/95, Technical Notes pp S34-S35.
10. 3 + H: 489.1300; Found: 489.1295.
11. HPLC method used a Hewlett Packard Model 1050 instrument and a Vydac C18 column (4.6 mm × 25 cm) at a flow rate of 1 ml/min with a gradient mobile phase from 2% B to 100% B over 45 min (A = 100% water with 0.1% TFA and B = 90% aqueous acetonitrile with 0.1 % TFA) monitored at 220 nm. Ret. time (min): 1, 11.33; 2, 14.01; 3, 7.65; 4, 15.85.
12. 2 + H: 791.2856; Found: 791.2859.