The first solid-phase synthesis of oligomeric α-aminooxy peptides

Synlett

Volumn , Issue 3, 2003, Pages 325-328

  Lee, Myung Ryul ^a   Lee, Jiyong ^a   Baek, Bong Hyeon ^a   Shin, Injae ^a  

^a Yonsei University   (South Korea)

Author keywords

Coupling; Deprotection; Solid support; Solid phase synthesis; aminooxy peptides

Indexed keywords

MONOMER; OLIGOMER; PEPTIDE DERIVATIVE;

ARTICLE; PROTECTION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID;

EID: 0037288239     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37127     Document Type: Article

References (23)

1. For a review: Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.
2. Yang, D.; Li, B.; Ng, F.-F.; Yan, Y.-L.; Qu, J.; Wu, Y.-D. J. Org. Chem. 2001, 66, 7303; and references are therein.
3. Baek, B.-h.; Lee, M.-r.; Kim, K. Y.; Cho, U.-I.; Boo, D. W.; Shin, I., manuscript in preparation.
4. Lee, M.-r.; Kim, K. Y.; Cho, U.-I.; Boo, D. W.; Shin, I., manuscript in preparation.
5. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149.
6. (a) Abele, S.; Guichard, G.; Seebach, D. Helv. Chim. Acta 1998, 81, 2141.
7. (b) Yuasa, H.; Kamata, Y.; Kurono, S.; Hashimoto, H. Bioorg. Med. Chem. Lett. 1998, 8, 2139.
8. (c) Hamper, B. C.; Kolodziej, S. A.; Scates, A. M.; Smith, R. G.; Cortez, E. J. Org. Chem. 1998, 63, 708.
9. (d) Malenfant, P. R. L.; Frechet, J. M. J. Chem. Commun. 1998, 2657.
10. (e) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556.
11. (f) Kim, J.-M.; Bi, Y.; Paikoff, S. J.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5305.
12. (g) Smith, J.; Liras, J. L.; Schneider, S. E.; Anslyn, E. V. J. Org. Chem. 1996, 61, 8811.
13. (h) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 16.
14. (i) Cho, C. Y.; Moran, E. J.; Cherry, S. R.; Stephans, J. C.; Fodor, S. P. A.; Adams, C. L.; Sundaram, A.; Jacobs, J. W.; Schultz, P. G. Science 1993, 261, 1303.
15. (j) Zuckermann, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646.
16. 6
17. (a) Shin, I.; Lee, M.-r.; Lee, J.; Jung, M.; Lee, W.; Yoon, J. J. Org. Chem. 2000, 65, 7667.
18. (b) Shin, I.; Lee, J. Synlett 2000, 1297.
19. (a) Lee, M.-r.; Lee, J.; Shin, I. Synlett 2002, 1463.
20. (b) Shin, I.; Park, K. Org. Lett. 2001, 4, 869.
21. Krchñák, V.; Vágner, J.; Lebl, M. Int. J. Peptide Protein Res. 1988, 32, 415.
22. Hancock, W. S.; Battersby, J. E. Anal. Biochem. 1976, 71, 260.
23. 3CN in water (0.1% TFA) over 40 min (flow rate, 1.0 mL/min). The digested Ac-Phe-Lys-OH and H-Phe-Leu-OH were eluted at 15.9 minutes and 17.9 minutes under the same elution conditions described above.