Comparative study of reductive amination reaction on 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid and its monomethoxy analog using the Multipin™ approach

Molecular Diversity

Volumn 4, Issue 3, 1998, Pages 155-163

  Bui, Chinh T ^a   Bray, Andrew M ^a   Pham, Yen ^a   Campbell, Rhonda ^a   Ercole, Francesca ^a   Rasoul, Firas A ^a   Maeji, N Joe ^a  

^a Migenix Inc   (United States)

Author keywords

Linkers; N alkylamides; Reductive amination; Solid phase synthesis

Indexed keywords

5 (4 FORMYL 3 METHOXYPHENOXY)VALERIC ACID; 5 (4 FORMYL 3,5 DIMETHOXYPHENOXY)VALERIC ACID; 5-(4-FORMYL-3,5-DIMETHOXYPHENOXY)VALERIC ACID; 5-(4-FORMYL-3-METHOXYPHENOXY)VALERIC ACID; BENZALDEHYDE DERIVATIVE; N PENTANOIC ACID; N-PENTANOIC ACID; PEPTIDE; VALERIC ACID DERIVATIVE;

AMINATION; ARTICLE; CHEMISTRY; COMPARATIVE STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; METABOLISM; SYNTHESIS;

AMINATION; BENZALDEHYDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; PENTANOIC ACIDS; PEPTIDES; VALERATES;

EID: 0032227722     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1009642429617     Document Type: Article

References (20)

1. Bunin, B.A. and Ellman, J.A., A general and expedient method for the solid-phase synthesis of 1,4-benzodiazepine derivatives, J. Am. Chem. Soc., 114 (1992) 10997-10998.
2. Bunin, B.A., Plunkett, M.J. and Ellman, J.A., The combinatorial synthesis and chemical and biological evaluation of a 1,4-benzodiazepine library, Proc. Natl. Acad. Sci. USA, 91 (1994)4708-4712.
3. James, I.W., Linkers for solid phase organic synthesis, Tetrahedron, 55 (1999) 4855-4946.
4. Albericio, F., Cordonier, N.K., Biancalana, S., Gera, L., Masada, R.I., Hudson, D. and Barany, G., Preparation and application of the 5-(4-(9-fluorenylmethyloxy-carbonyl)aminomethyl-3,5-dimethoxyphenoxy)-valeric acid (PAL) handle for the solid phase synthesis of C-terminal peptide amides under mild conditions, J. Org. Chem., 55 (1990) 3730-3743.
5. Songster, M.F., Vagner, J. and Barany, G., Acid-labile handles for Fmoc solid-phase synthesis of peptide N-alkylamides, Lett. Pept. Sci., 2 (1995) 265-270.
6. Albericio, F. and Barany, G., An acid-labile anchoring linkage for solid-phase synthesis of C-terminal peptide amides under mild conditions, Int. J. Pept. Protein Res., 30 (1987) 206-216.
7. Gray, S.N., Kwon, S. and Schultz, P.G., Combinatorial synthesis of 2,9-substituted purines, Tetrahedron Lett., 38 (1997) 1161-1164.
8. Boojamra, C.G., Burow, K.M. and Ellman, J.A., An expedient and high-yield method for the solid phase synthesis of diverse 1,4-benzodiazozepine-2,5-diones, J. Org. Chem., 60 (1995) 5742-5743.
9. Fivush, M.A. and Willson, T.M., AMEBA: An acid sensitive aldehyde resin for solid phase synthesis, Tetrahedron Lett., 38 (1997)7151-7154.
10. Sarantakis, D. and Bickksler, J.J., Solid phase synthesis of secamides and removal from the polymeric support under mild conditions, Tetrahedron Lett., 38 (1997) 7325-7328.
11. Swayze, E.E., Secondary amide-based linkers for solid phase organic synthesis, Tetrahedron Lett., 38 (1997) 8465-8468.
12. Maeji, N.J., Valerio, R.M., Bray, A.M., Campbell, R.A. and Geysen, H.M., Grafted supports used with the Multipin method of peptide synthesis, React. Polym., 22 (1994) 203-212.
13. The optimization (two-step reductive animation reaction) has been studied with three variables: solvents (DMP, DCM, THF), temperature (25 °C and 60 °C), duration (2 h and 16 h), and the optimal condition was described in the Experimental section.
14. Gordon, D.W. and Steele, J., Reductive alkylation on a solid phase: Synthesis of a piperazinedione combinatorial library, Bioorg. Med. Chem. Lett., 5 (1995) 47-50.
15. Khan, N.M., Arumugam, V. and Balasubramanian, S., Solid phase reductive alkylation of secondary amines, Tetrahedron Lett., 37 (1996) 4819-4822.
16. The optimization (one-step reductive amination reaction) has been studied with two variables: temperature (25 °C and 60 °C) and duration (2 h and 16 h), and the optimal condition was described in the Experimental section.
17. Reverse phase high performance liquid chromatography (RPHPLC) was conducted with Rainin, Microsorb-MV Cat.# 86-200-F3, 50×4.6 mm column using gradient mobile-phase 0-100% B over 11.5 min. Flow rate: 1.5 ml/min (solvent A: 0.1% ortho-phosphoric acid in water; solvent B: 0.1% orthophosphoric acid in 90% acetonitrile). Detection: 214 nm.
18. Mass spectrometric analysis (MS): electrospray ES-MS was conducted with a Perkin-Elmer Sciex API III using 0.1% acetic acid in 60% acetonitrilec.
19. Bray, A.M., Maeji, J., Valerio, R.A., Campbell, R.A. and Geysen, H.M., Direct cleavage of peptides from a solid support into aqueous buffer. Application in simultaneous multiple peptide synthesis, J. Org. Chem., 56 (1991) 6659-6666.
20. Abdel-Magid, A.F., Carson, K.G., Harris, B.D., Maryanoff, C. A. and Shah, R.D., Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedure, J. Org. Chem., 61 (1996) 3849-3862.