The synthesis of a geminally perfluoro-tert-butylated β-amino acid and its protected forms as a potential pharmacokinetic modulator and reporter for peptide-based pharmaceuticals

Journal of Organic Chemistry

Volumn 72, Issue 4, 2007, Pages 1464-1467

  Jiang, Zhong Xing ^a   Yu, Y Bruce ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG PRODUCTS; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE; PHARMACOKINETICS; POLYPEPTIDES; SYNTHESIS (CHEMICAL);

PHARMACOKINETIC MODULATORS; REVERSED PHASE CHROMATOGRAPHY; SOLID PHASE CHEMISTRY; WATER PARTITION MEASUREMENT;

AMINO ACIDS;

AMINO ACID DERIVATIVE; BETA AMINO ACID; OCTANOL; PEPTIDE DERIVATIVE; PERFLUORO COMPOUND; WATER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS; REVERSED PHASE LIQUID CHROMATOGRAPHY; SOLID;

FLUOROCARBONS; PEPTIDES; PROTEIN CONFORMATION;

EID: 33846944710     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0616308     Document Type: Article

References (14)

1. Hsieh, K.-H.; Needleman, P.; Marshall, G. R. J. Med. Chem. 1987, 30, 1097-1100.
2. (a) Ortial, S.; Durand, G.; Poeggeler, B.; Polidori, A.; Pappolla, M. A.; Böker, J.; Hardeland, R.; Pucci, B. J. Med. Chem. 2006, 49, 2812-2820.
3. (b) Perino, S.; Contino-Pépin, C.; Jasseron, S.; Rapp, M.; Maurizis, J.-C.; Pucci, B. Bioorg. Med. Chem. Lett. 2006, 16, 1111-1114.
4. (c) Park, B. K.; Kitteringham, N. R.; O'Neill, P. M. Ann. Rev. Pharmacol. Toxicol. 2001, 41, 443-470.
5. (d) Gerebtzoff, G.; Li-Blatter, X.; Fischer, H.; Frentzel, A.; Seelig, A. ChemBioChem 2004, 5, 676-684.
6. Wolf, W.; Presant, C. A.; Waluch, V. Adv. Drug Delivery Rev. 2000, 41, 55-74.
7. (a) Yu, Y.; Monera, O. D.; Hodges, R. S.; Privalov, P. L. J. Mol. Biol. 1996, 255, 367-372.
8. (b) Yu, Y.; Monera, O. D.; Hodges, R. S.; Privalov, P. L. Biophys. Chem. 1996, 59, 299-314.
9. Kovacs, J. M.; Mant, C. T.; Hodges, R. S. Biopolymers 2006, 84, 283-297.
10. Aguilera, B.; Romero-Ramirez, L.; Abad-Rodriguez, J.; Corrales G.; Nieto-Sampedro, M.; Fernandez-Mayoralas, A. J. Med. Chem. 1998, 41, 4599-4606.
11. Sebesta, D. P.; O'Rourke, S. S.; Pieken, W. A. J. Org. Chem. 1996, 61, 361-362.
12. Chan, W. C.; White, P. D. Fmoc Solid Phase Peptide Synthesis: A Practical Approach; Oxford University Press: New York, 2000; pp 1-75.
13. (a) Abbruscato, T.; Williams, S.; Misicka, A.; Lipkowski, A. W.; Hryby, V. J.; Davis, T. P. J. Pharmacol. Exp. Ther. 1996, 276, 1049-1057.
14. (b) Gentry, C. L.; Egleton, R. D.; Gillespie, T.; Abbruscato, T. J.; Bechowski, H. B.; Hruby, V. J.; Davis, T. P. Peptides 1999, 20, 1229-1238.