Synthesis of glyoxylyl peptides using a phosphine labile α,α′-diaminoacetic acid derivative

Tetrahedron Letters

Volumn 45, Issue 38, 2004, Pages 7163-7165

  Far, Samia ^a   Melnyk, Oleg ^a  

^a UNIV LILLE   (France)

Author keywords

Oxo aldehyde; Peptide; Phosphine

Indexed keywords

AMINO ACID DERIVATIVE; GLYCINE; GLYOXYLIC ACID; PEPTIDE DERIVATIVE; PHOSPHINE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; DEPROTECTION REACTION; PROTEIN DEGRADATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS;

EID: 4444332560     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.038     Document Type: Article

References (7)

1. O. Melnyk, J.-A. Fehrentz, J. Martinez, and H. Gras-Masse Peptide Sci. 55 2000 165 186
2. S. Far, and O. Melnyk Tetrahedron Lett. 45 2004 1271 1273
3. E. Wünsch, L. Moroder, and S. Romani Hoppe- Seyler’s Z. Physiol. Chem. 363 1982 1461 1464
4. G.B. Fields, and R.L. Noble Int. J. Pept. Protein Res. 35 1990 161 214
5. E.B. Getz, M. Xiao, T. Chakrabarty, R. Cooke, and P.R. Selvin Anal. Biochem. 273 1999 73 80
6. Typical deprotection procedure: the peptide (3.0 Iμmol) was dissolved in 5 mL of 0.1 M Trisa-HCl buffer (pH 8.33). Tris(2-carboxyethyl)phosphine hydrochloride (86 mg, 0.3 mmol, 100 equiv) was added and the mixture was stirred at room temperature for 21 h. Aliquots (95 μL) of the reaction mixture were mixed with 5 μL of acetic acid and injected on a C18 Delta Pak column (3.9 A×- 300 mm, experimental conditions specified in Fig. 1) for HPLC monitoring
7. K.F. Geoghegan, and J.G. Stroh Bioconjugate Chem. 3 1992 138 146