4-alkoxy-2-hydroxybenzaldehyde (AHB): A versatile aldehyde linker for solid-phase synthesis of C-terminal modified peptides and peptidomimetics

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1787-1790

  Okayama, Toru ^a   Burritt, Andrew ^a,b   Hruby, Victor J ^a  

^a University of Arizona   (United States)

^b SIDDCO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE;

ARTICLE; BIOCHEMISTRY; CHEMISTRY; METHODOLOGY; MOLECULAR MIMICRY; SYNTHESIS;

BIOCHEMISTRY; MOLECULAR MIMICRY; PEPTIDES;

EID: 0034729606     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000048h     Document Type: Article

References (11)

1. a) Songster, M. F.; Vagner, J.; Barany, G. Lett. Pept. Sci. 1996, 2, 265.
2. (b) Boojamra, C. G.; Burrow, K. M.; Ellman, J. A. J. Org. Chem. 1995, 60, 5742.
3. (c) Sarantakis, D.; Bickslar, J. J. Tetrahedron Lett. 1997, 38, 7325.
4. (d) Bourne, G. T.; Meutermans, P. F.; Alewood, R. P.; McGeary, R. P.; Scanlon, M.; Watson, A. A.; Smythe, M. L. J. Org. Chem. 1999, 64, 3095.
5. Johnston, T.; Quibell, M.; Owen, D.; Sheppard, R. C. J. Chem. Soc., Chem. Commun. 1993, 369.
6. Resins used were purchased from Calbiochem-Novabiochem Corp., CA
7. 5: C, 58.93; H, 5.39. Found: C, 58.70; H, 5.4 7.
8. The loading level of the aldehyde linker onto the aminomethylated resin was determined from the quantitative HPLC analysis of Bz-Gly-NHEt obtained by method A in Scheme 1 based on the substitution level of the aminomethylated polystyrene used.
9. 2/TMOF generally gave good results.
10. Jensen, K. J.; Alsina, J.; Songster, M. F.; Vágner, J.; Albericio, F.; Barany, G. J. Am. Chem. Soc. 1998, 120, 5441.
11. Misicka, A.; Lipkowski, A. W.; Horvath, R.; Davis, P.; Porreca, F.; Yamamura, H. I.; Hruby, V. J. Life Sci. 1997, 60, 1263.