Biotin and fluorescein labeling of biomolecules by active esters of 1-phenylpyrazolin-5-ones

Tetrahedron Letters

Volumn 37, Issue 25, 1996, Pages 4313-4316

  Kremsky, Jonathan N ^a,b   Pluskal, Malcolm ^a,c   Casey, Shelagh ^a   Perry O'keefe, Heather ^a   Kates, Steven A ^a   Sinha, Nanda D ^a,c  

^a PERKINELMER INC   (United States)

^b Prime Organics Inc   (United States)

^c Unisyn Technologies Inc ^*  (United States)

Author keywords

Biotin; Fluorescein; Labeling; Oligonucleotides; Peptide; PNA; Probes

Indexed keywords

AMINE; BIOPOLYMER; BIOTIN; ESTER; FLUORESCEIN; NUCLEIC ACID; OLIGONUCLEOTIDE; PEPTIDE; PYRAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL LABELING; CHEMICAL REACTION; CHEMICAL STRUCTURE; DERIVATIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEOTIDE SEQUENCE; POLYACRYLAMIDE GEL ELECTROPHORESIS; SYNTHESIS;

EID: 0029946225     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00833-7     Document Type: Article

References (20)

1. th American Chemical Society Northeast Regional Meeting, Burlington, VT, June 19-22, 1994.
2. Amino acids and peptides are abbreviated and designated following rules of the IUPAC-IUB Commission of Biochemical Nomenclature in J. Biol. Chem. 1972, 247, 977. Additionally, the following abbreviations are used: Al, allyl; BHA, benzhydrylamine; Boc, tert.-butyloxycarbonyl; tBu, tert.-butyl; Bz, benzoyl; DCC, N,N′-dicyclohexylcarbodiimide; DIEA, N,N-diisopropylethylamine; DMAP, 4-dimethylamino pyridine; DMF, N,N-dimethylformamide; DMT, 4,4′-dimethoxytrityl; DMTCl, 4,4′-dimethoxytrityl chloride; DNA, deoxyribonucleic acid; Fmoc, 9-fluorenylmethyloxycarbonyl; HATU, 0-(7-azabenzotriazol1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; HOAc, acetic acid; HOBt, 1-hydroxybenzotriazole; Hpp, 1-(4′-nitrophenyl)-pyrazol-5-one; HPLC, high performance liquid chromalography; MALDI-TOF, matrix assisted laser desorption ion time-of flight mass spectrometry,; NMM, N-methylmorpholine; NMP, N-methylpyrrolidinone; PAGE, polyacrylamide gel electrophoresis; PAL, 5-(4-Fmoc-aminomethyl-3,5-dimethoxyphenoxy)valeric acid; PEG, polyethylene glycol; PNA, peptide nucleic acid; PS, polystyrene, TFA, trifluoroacetic acid; TFMSA, trifluoromethanesulfonic acid; Xpp, 4-substituted 1-phenylpyrazolin-5-one. Amino acid symbols denote the L-configuration unless indicated otherwise.
3. For a recent review, see: (a) Gallop, M.A., Barrett, R.W., Dower, R.J., Fodor, S.P.A., Gordon, E.M. J. Med. Chem. 1994, 37, 1233.
4. (b) Gordon, E.M., Barret, R.W., Dower, R.J., Fodor, S.P.A., Gallop, M.A. J. Med. Chem. 1994, 37, 1385.
5. Keller, G.H. and Manak, M.M. DNA Probes, Ch.4 &5, Macmillan Publishers, Ltd., U.K. 1989.
6. (a) Hudson, D., U.S. Patent 1993, 5, 233, 044.
7. (b) Hudson, D. In "Peptides: Chemistry, Structure and Biology, Proceedings of the 11th American Peptide Symposium (I.E. Rivier. and G.Marshall, eds.), Escom, Leiden, 1990, 914.
8. (c) Hudson, D. Peptide Res. 1990, 3, 51.
9. 2H).
10. Zhang, G. and Case, R. U.S. Patent No. 5, 128, 476 (1992).
11. 2Ar); mp 125-129 °C.
12. Theisen, P., McCollum, C., Upadhya, K., Jacobson, K., Vu, H. and Andrus, A. Tetrahedron Lett. 1992, 33, 5033.
13. 3); mP 140-144 °C.
14. Sinha, N.D., Biernat, J., McManus, J., Koester, H. Nucleic Acids Res. 1984, 12, 4539.
15. 3CN, 1:0 to 1:9 in 30 min.
16. Christensen, L., Fitzpatrick, R., Gildea, B., Warren, W. and Coull, J. In "Innovation and Perspectives in Solid Phase Synthesis and Complementary Technologies - Biological and Biomedical Applications" (Epton, R., Ed) Mayflower Worldwide Limited, Birmingham, 1994, 149.
17. + biotinylated PNA 5956.3 (calcd. 5954.7).
18. Perry-O'Keefe, H. and Kissinger, C.M. In "Current Protocols in Molecular Biology" (Ausubel, F.M., et al. Eds.) John Wiley, New York, 1992, Suppl. 20, 3.19-1.
19. Albericio, F., Kneib-Cordonier, N., Biancalana, S., Gera, L., Maseda, I., Hudson, D. and Barany, G. J. Org. Chem. 1990, 55, 3730.
20. + 1421 (calcd. 1419).