Photoaffinity-labeled peptoids and depsipeptides by multicomponent reactions

Synthesis

Volumn , Issue 17, 2010, Pages 2997-3003

  Henze, Michael ^a   Kreye, Oliver ^a   Brauch, Sebastian ^a   Nitsche, Christoph ^a   Naumann, Kai ^a   Wessjohann, Ludger A ^a,b   Westermann, Bernhard ^a,b  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

Passerini reaction; peptoids; photo leucine; photo methionine; Ugi reaction

Indexed keywords

PASSERINI REACTION; PEPTOIDS; PHOTO-LEUCINE; PHOTO-METHIONINE; UGI REACTION;

AMINO ACIDS;

1 [[4 [[(BENZYLOXY)CARBONYL]AMINO]BUTYL]CARBONYL] 2 METHYLETHYL 3 (PHENYLCARBONYL)BENZOATE; 1 BENZYL 2 (BUTYLAMINO) 2 OXOETHYL 3 (METHYL 3H DIAZIREN 3 YL)PROPANOATE; 1 BENZYL 2 (BUTYLAMINO) 2 OXOETHYL 3 (PHENYLCARBONYL)BENZOATE; 2 (3 METHYL 3H DIAZIREN 3 YL)ETHANOL; 2 (3 METHYL 3H DIAZIREN 3 YL)ETHYL 4 TOLUENESULFONATE; 2 OXO 1 BENZYL 2 [[4 (PHENYLCARBONYL)PHENYL]AMINO]ETHYLBENZOATE; 3 (3 METHYL 3H DIAZIREN 3 YL)PROPANENITRILE; 3 (3 METHYL 3H DIAZIREN 3 YL)PROPANOIC ACID; BENZOPHENONE; BENZYL 3 (BUTYLAMINO) 2 [(3 METHYL 3H 1,2 DIAZIREN 3 YL)METHYL] 3 OXOPROPANOATE; BENZYL 4 ISOCYANOBUTYLCARBAMATE; BENZYL [4 (CYCLOHEXYLAMINO)] 3 [[(3 METHYL 3H DIAZIREN 3 YL)METHYL] 2,4 DIOXOBUTYL]CARBAMATE; BENZYL [4 [[N BENZYL N [[3 (PHENYLCARBONYL)PHENYL]CARBONYL]VALYL]AMINO]BUTYL]CARBAMATE; DEPSIPEPTIDE; DIAZIRINE; LEUCINE; METHIONINE; N (4 BENZOYL)PHENYL ISOCYANIDE; N [(BENZYLOXY)CARBONYL]GLYCYL N BENZYL N [4 (PHENYLCARBONYL)PHENYL]VALINAMIDE; N [2 (2,2 DIMETHOXYETHYL)PHENYL] N (1 METHYLETHYL) N [[3 (PHENYLCARBONYL)PHENYL]CARBONYL]PHENYLALANINAMIDE; N [2 (2,2 DIMETHOXYETHYL)PHENYL] N [3 (3 METHYL 3H DIAZIREN 3 YL)PROPANOYL] N (1 METHYLETHYL)VALINAMIDE; N BENZYL N BUTYL N [3 (3 METHYL 3H DIAZIREN 3 YL)PROPANOYL]VALINAMIDE; N CYCLOHEXYL N [3 (3 METHYL 3H DIAZIREN 3 YL)PROPANOYL] N (1 METHYLETHYL)PHENYLALANINAMIDE; PEPTOID; PHENYL 3 [[4 [[(BENZYLOXY)CARBONYL]AMINO]BUTYL]AMINO] 2 [(3 METHYL 3H DIAZIREN 3 YL)METHYL] 3 OXOPROPANOATE; UNCLASSIFIED DRUG;

AFFINITY LABELING; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CLINICAL PROTOCOL; CROSS LINKING; DEHYDRATION; MOLECULAR PROBE; MULTICOMPONENT REACTION; OXIDATION; PASSERINI REACTION; PHOTOAFFINITY; PURIFICATION; SYNTHESIS; UGI REACTION;

EID: 77956049345     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258182     Document Type: Article

References (23)

1. Kawakami T, Murakami H, Suga H, J. Am. Chem. Soc. 2008 130 16861
2. Masip I, Pérez-Payá E, Messeguer A, Comb. Chem. High Throughput Screening 2005 8 235
3. Shah N H., Butterfoss G L., Nguyen K, Yoo B, Bonneau R, Rabenstein D L., Kirshenbaum K, J. Am. Chem. Soc. 2008 130 16622
4. Zuckermann R N., Kodadek T, Curr. Opin. Mol. Ther. 2009 11 299
5. Kwon Y U., Kodadek T, J. Am. Chem. Soc. 2007 129 1508
6. Domling A, Chem. Rev. 2006 106 17; and references cited therein
7. Fowler S A., Blackwell H E., Org. Biomol. Chem. 2009 7 1508; and references cited therein
8. Gorske B C., Stringer J R., Bastian B L., Blackwell H E., J. Am. Chem. Soc. 2009 131 16555; and references cited therein
9. Wang H X., Nakata E, Hamachi I, ChemBioChem 2009 10 2560
10. Collet M, Lenger J, Jenssen K, Plattner H P., Sewald N, J. Biotechnol. 2007 129 316
11. Song Z Q., Zhang Q S., Org. Lett. 2009 11 4882
12. Hulme C, Dietrich J, Mol. Diversity 2009 13 195
13. Wessjohann L A., Rivera D G., Vercillo O E., Chem. Rev. 2009 109 796
14. Jiao C Y., Alves I D., Point V, Lavielle S, Sagan S, Chassaing G, Bioconjugate Chem. 2010 21 352
15. Fleming S A., Tetrahedron 1995 51 1249
16. Suchanek M, Radzikowska A, Thiele C, Nature Meth. 2005 2 261
17. Durek T, Zhang J, He C, Kent S B. H., Org. Lett. 2007 9 5497
18. Sieber S A., Niessen S, Hoover H S., Cravatt B F., Nature Chem. Biol. 2006 2 274
19. Church R F. R., Weiss M J., J. Org. Chem. 1970 35 2465
20. Ngouansavanh T, Zhu J P., Angew. Chem. Int. Ed. 2006 45 3495
21. Kreye O, Westermann B, Wessjohann L A., Synlett 2007 3188
22. Kuhn C. S, Lehmann J, Sandhoff K, Bioconjugate Chem. 1992 3 230
23. Pittelkow M, Lewinsky R, Christensen J B., Synthesis 2002 2195