Solid-phase synthesis of (ω-Aminoalkyl)peptoids using azide chemistry

Synlett

Volumn , Issue 10, 2010, Pages 1544-1548

  Fritz, Daniel ^a   Bräse, Stefan ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

Amines; Azides; Microwave synthesis; Peptidomimetic transporters; Peptoid; Protecting groups; Solid phase synthesis

Indexed keywords

ALKANE DERIVATIVE; AZIDE; BROMOACETIC ACID; MACROGOL; N,N DIMETHYLFORMAMIDE; PEPTIDOMIMETIC AGENT; PEPTOID; TETRAHYDROFURAN;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENANTIOMER; HYDROLYSIS; HYDROPHOBICITY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MICROWAVE RADIATION; MOLECULAR PROBE; SOLID PHASE SYNTHESIS;

EID: 77953252974     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219925     Document Type: Article

References (37)

1. Simon R J., Kania R S., Zuckermann R N., Huebner V D., Jewell D A., Banville S, Ng S, Wang L, Rosenberg S, Marlowe C K., Proc. Natl. Acad. Sci. U.S.A. 1992 89 9367
2. Zuckermann R, Dubois-Stringfellow N, Dwarki V, Innis M A., Murphy J E., Cohen F, Tetsuo U, (Chiron Corporation, USA) PCT Int. Appl. WO 9806437 1998
3. Peretto I, Sanchez-Martin R M., Wang X.-h, Ellard J, Mittoo S, Bradley M, Chem. Commun. 2003 2312
4. Diaz-Mochon J J., Fara M A., Sanchez-Martin R M., Bradley M, Tetrahedron Lett. 2008 49 923
5. Fara M A., Diaz-Mochon J J., Bradley M, Tetrahedron Lett. 2006 47 1011
6. Schröder T, Niemeier N, Afonin S, Ulrich A S., Krug H F., Bräse S, J. Med. Chem. 2008 51 376
7. Schröder T, Schmitz K, Niemeier N, Balaban T S., Krug H F., Schepers U, Bräse S, Bioconjugate Chem. 2007 18 342
8. Tan N C., Yu P, Kwon Y.-U, Kodadek T, Bioorg. Med. Chem. 2008 16 5853
9. For a different approach, see:, Hahn F, Schmitz K, Balaban T S., Bräse S, Schepers U, ChemMedChem 2008 3 1185
10. Zuckermann R N., Kerr J M., Kent S B. H., Moos W H., J. Am. Chem. Soc. 1992 114 10646
11. For a review concerning azide chemistry, see:, Bräse S, Gil C, Knepper K, Zimmermann V, Angew. Chem. Int. Ed. 2005 44 5188
12. Angew. Chem. 2005, 117, 5320
13. Jang H, Fafarman A, Holub J M., Kirshenbaum K, Org. Lett. 2005 7 1951
14. Holub J M., Jang H, Kirshenbaum K, Org. Biomol. Chem. 2006 4 1497
15. Shin S B. Y., Yoo B, Todaro L J., Kirshenbaum K, J. Am. Chem. Soc. 2007 129 3218
16. Holub J M., Jang H, Kirshenbaum K, Org. Lett. 2007 9 3275
17. Holub J M., Garabedian M J., Kirshenbaum K, QSAR Comb. Sci. 2007 26 1175
18. Shah N H., Kirshenbaum K, Macromol. Rapid Commun. 2008 29 1134
19. Lim H.-S, Archer C T., Kim Y.-C, Hutchens T, Kodadek T, Chem. Commun. 2008 1064 See also:, Disney M D., PCT Int. Appl. WO 20081034898 2008
20. Lee J W., Jun S I., Kim K, Tetrahedron Lett. 2001 42 2709
21. +; HRMS: m / z calcd: 229.1453; found: 229.1449. 2-[2-(2-Azidoethoxy)ethoxy]ethylamine (3d): Analytical data are consistent with those reported by:, Klein E, DeBonis S, Thiede B, Skoufias D A., Kozielski F, Lebeau L, Bioorg. Med. Chem. 2007 6474
22. The final products were isolated as ammonium trifluoroacetate salts
23. For a different approach, see:, Natarajan A, Du W, Xiong C.-Y, DeNardo G L., DeNardo S J., Gervay-Hague J, Chem. Commun. 2007 695
24. Feau C, Klein E, Kerth P, Lebeau L, Bioorg. Med. Chem. Lett. 2007 17 1499
25. Olivos H J., Alluri P G., Reddy M M., Salony D, Kodadek T, Org. Lett. 2002 4 4057
26. Gorske B C., Jewell S A., Guerard E J., Blackwell H E., Org. Lett. 2005 7 1521
27. Bartra M, Urpí F, Vilarrasa J, Tetrahedron Lett. 1987 28 5941
28. For general scope and limitation of this reagent, see:, Bartra M, Romea P, Urpí F, Vilarrasa J, Tetrahedron 1990 46 587
29. For its application on solid supports, see:, Zimmermann V, Avemaria F, Bräse S, [nl] J. Comb. Chem. 2007 9 200
30. Kirshenbaum K, Barron A E., Goldsmith R A., Armand P, Bradley E K., Truong K T. V., Dill K A., Cohen F E., Zuckermann R N., Proc. Natl. Acad. Sci. U.S.A. 1998 95 4303
31. For the only report of PEG-type side chains in peptoids according to CAS, see:, Barron A E., PCT Int. Appl. [nl]WO 2000043547 2000
32. Alkoxyethyl peptoids displaying PEG-like properties such as resistance to biofouling are known, for examples, see
33. Kim J M., Roy R, Carbohydr. Lett. 1996 1 465
34. Huang C.-Y, Uno T, Murphy J E., Lee S, Hamer [nl]J D., Escobedo J A., Cohen F E., Radhakrishnan R, Dwarki V, Zuckermann R N., Chem. Biol. 1998 5 345
35. Statz A R., Park J P., Chongsiriwatana N P., Barron A E., Messersmith P B., Biofouling 2008 24 439
36. Statz A R., Barron A E., Messersmith P B., Soft Matter 2008 4 131
37. Adamczyk M, Grote J, Synth. Commun. 2001 31 2681