N,N,N′,N′-tetramethylchloroformamidinium hexafluorophosphate (TCFH), a powerful coupling reagent for bioconjugation

Bioconjugate Chemistry

Volumn 19, Issue 10, 2008, Pages 1968-1971

  Tulla Puche, Judit ^a   Torres, Ángela ^b   Calvo, Pilar ^d   Royo, Miriam ^b   Albericio, Fernando ^a,c  

^a INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^b Barcelona Science Park   (Spain)

^c UNIVERSITY OF BARCELONA   (Spain)

^d PHARMAMAR S A   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS;

ANTITUMORAL AGENTS; BIO-CONJUGATION; COUPLING PROCEDURE; COUPLING REAGENTS; DELIVERY VEHICLE; ESTER PRODRUG; HEXAFLUOROPHOSPHATES; PHARMACEUTICAL AGENTS; PRODRUGS;

ORGANIC COMPOUNDS;

N,N,N',N' TETRAMETHYLCHLOROFORMAMIDINIUM HEXAFLUOROPHOSPHATE; REAGENT; THIOCORALINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONJUGATION; DRUG SOLUBILITY; DRUG STRUCTURE; ESTERIFICATION; REACTION ANALYSIS;

EID: 55249114137     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc8002327     Document Type: Article

References (21)

1. Stella, V. J., and Nti-Addae, K. W. (2007) Prodrug strategies to overcome poor water solubility. Adv. Drug Delivery Rev. 59, 677-694.
2. Liederer, B. M., and Borchardt, R. T. (2006) Enzymes involved in the bioconversion of ester-based prodrugs. J. Pharm. Sci. 95, 1177-1195.
3. Stella, V. J. (2004) Prodrugs as therapeutics. Expert Opin. Ther/Pat. 14, 277-280.
4. Routio, J., Kumpulainen, H., Heimbach, T., Oliyai, R., Oh, D., Järvinen, T., and Savolainen, J. (2008) Prodrugs: design and clinical applications. Nat. Rev. 7, 255-270.
5. Beaumont, K., Webster, R., Gardner, I., and Dack, K. (2003) Design of ester prodrugs to enhance oral absorption of poorly permeable compounds: challenges to the discovery scientist. Curr. Drug Metab. 4, 461-485.
6. Li, C., Yu, D. F., Newman, R. A., Cabral, F., Stephens, L. C., Hunter, N., Milas, L., and Wallace, S. (1998) Complete regression well-established tumors using a novel water soluble poly(L-glutamic acid)-paclitaxel conjugate. Cancer Res. 58, 2404-2409.
7. Greco, F., and Vicent, M. J. (2008) Polymer-drug conjugates: current status and future trends. Front. Biosci. 13, 2744-2756.
8. Abuchowski, A., McCoy, J. R., Palczuk, N. C., van Es, T., and Davis, F. F. (1977) Effect of covalent attachment of polyethylene glycol on immunogenicity and circulating life of bovine liver catalase. J. Biol. Chem. 252, 3582-3586.
9. Veronese, F. M., and Pasut, G. (2005) PEGylation, successful approach to drug delivery. Drug Discovery Today 10, 1451-1458.
10. Greenwald, R. B., Choe, Y. H., McGuire, J., and Conover, C. D. (2003) Effective drug delivery by PEGylated drug conjugates. Adv. Drug Deliveryv. 55, 217-250.
11. Romero, F., Espliego, F., Pérez Baz, J., García de Quesada, T., Gravalos, D., De la Calle, F., and Fernández-Puentes, J. L. (1997) Thiocoraline, a new depsipeptide with antitumor activity produced by a marine Micromonospora. I. Taxonomy, fermentation, isolation, and biological activities. J. Antibiot. 50, 734-737.
12. Pérez Baz, J., Cañedo, L. M., Fernández Puentes, J. L., and Silva Elipe, M. V. (1997) Thiocoraline, a novel depsipeptide with antitumor activity produced by a marine Micromonospora. II. Physico-chemical properties and structure determination. J. Antibiot. 50, 738-741.
13. Carpino, L. A., and El-Faham, A. (1995) Tetramethylfluoroformamidinium hexafluorophosphate: a rapid-acting peptide coupling reagent for solution and solid phase peptide synthesis. J. Am. Chem. Soc. 117, 5401-5402.
14. Kaduk, C., Wenschuh, H., Beyerman, M., Forner, K., Carpino, L. A., and Bienert, M. (1996) Synthesis of Fmoc-amino acid fluorides via DAST, an alternative fluorinating agent. Lett. Pept. Sci. 2, 285-288.
15. Diago-Meseguer, J., Palomo-Coll, A. L., Fernández-Lizarbe, J. R., and Zugaza-Bilbao, A. (1980) A new reagent for activating carboxyl groups: preparation and reactions of N,N-bis[2-oxo-3-oxazolidinyl] phosphorodiamidic chloride. Synthesis 547-551.
16. (a) Kalir, R., Warshawsky, A., Fridkin, M., and Patchornik, A. (1975) New useful reagents for peptide synthesis. Insoluble active esters of polystyrene-bound 1-hydroxybenzotriazole. Eur. J. Biochem. 59, 55-61.
17. (b) Mokotoff, M., and Patchornik, A. (1983) Synthesis of the C-terminal half of thymosin α1 by the polymeric reagent method. Int. J. Pept. Protein Res. 21, 145-154.
18. Pop, I. E., Deprez, B. P., and Tartar, A. L. (1997) Versatile acylation of N-Nucleophiles using a new polymer-supported 1-hydroxybenzotriazole derivative. J. Org. Chem. 62, 2594-2603.
19. Blankemeyer-Menge, B., Nimtz, M., and Frank, R. (1990) An efficient method for anchoring Fmoc-amino acids to hydroxyl-functionalized solid supports. Tetrahedron Lett. 31, 1701-1704.
20. Vendrell, M., Ventura, R., Ewenson, A., Royo, M., and Albericio, F. (2005) N-[Chloro(dimethylamino)methylene]-N-methylmethanaminium chloride (TMUC Cl), the reagent of choice for the solid-phase synthesis of anilides. Tetrahedron Lett. 46, 5383-5386.
21. Barlos, K., Gatos, D., Kallitsis, J., Papaphotiu, G., Sotiriu, P., Yao, W., and Schaefer, W. (1989) Preparation of protected peptide fragments using triphenylmethyl resins. Tetrahedron Lett. 30, 3943-3946.