Aziridine-2-carboxylic acid-containing peptides: Application to solution- and solid-phase convergent site-selective peptide modification

Journal of the American Chemical Society

Volumn 127, Issue 20, 2005, Pages 7359-7369

  Galonić, Danica P ^a   Ide, Nathan D ^a   Van Der Donk, Wilfred A ^a   Gin, David Y ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AMINO ACIDS; CARBOXYLIC ACIDS; CHEMICAL MODIFICATION; SYNTHESIS (CHEMICAL);

AZIRIDINES; BIOCHEMICAL TAGS; CHEMICAL LIGATION; SITE-SELECTIVE CONJUGATION;

POLYPEPTIDES;

AZIRIDINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; PEPTIDE;

ANALYTIC METHOD; ARTICLE; EUKARYOTIC CELL; GLYCOSYLATION; PEPTIDE ANALYSIS; PROTEIN MODIFICATION; SAMPLING; SOLID PHASE EXTRACTION; STEREOCHEMISTRY;

AZIRIDINES; GLYCOPEPTIDES; PEPTIDES; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SULFHYDRYL COMPOUNDS;

EID: 19744362073     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050304r     Document Type: Article

References (89)

1. (a) Kadereit, D.; Kuhlmann, J.; Waldmann, H. ChemBioChem. 2000, 1, 144-169.
2. (b) Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357-2364.
3. (c) Rudd, P. M.; Elliott, T.; Cresswell, P.; Wilson, I. A.; Dwek, R. A. Science 2001, 291, 2370-2376.
4. (d) Seitz, O.; Heinemann, I.; Mattes, A.; Waldmann, H. Tetrahedron 2001, 57, 2247-2277.
5. (a) Seitz, O. ChemBioChem. 2000, 1, 214-246.
6. (b) Grogan, M. J.; Pratt, M. R.; Marcaurelle, L. A.; Bertozzi, C. R. Annu. Rev. Biochem. 2002, 71, 593-634.
7. Vojtek, A. B.; Der, C. J. J. Biol. Chem. 1998, 273, 19925-19928.
8. (a) Meldal, M.; St Hilaire, P. M. Curr. Opin. Chem. Biol. 1997, 1, 552-563.
9. (b) Slovin, S. F.; et al. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 5710-5715.
10. (c) Wong, C.-H. Acc. Chem. Res. 1999, 32, 376-385.
11. (a) Sames, D.; Chen, X.-T.; Danishefsky, S. J. Nature 1997, 389, 587-591.
12. (b) Danishefsky, S. J.; Allen, J. R. Angew. Chem., Int. Ed. 2000, 39, 836-863.
13. (c) Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4537.
14. (d) Keil, S.; Claus, C.; Dippold, W.; Kunz, H. Angew. Chem., Int. Ed. 2001, 40, 366-369.
15. (a) Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390.
16. (b) Hang, H. C.; Bertozzi, C. R. Acc. Chem. Res. 2001, 34, 727-736.
17. (c) Zhu, Y.; van der Donk, W. A. Org. Lett. 2001, 3, 1189-1192.
18. (d) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543.
19. (e) Davis, B. G. Chem. Rev. 2002, 102, 579-602.
20. (f) Galonić, D. P.; van der Donk, W. A.; Gin, D. Y. Chem. Eur. J. 2003, 9, 5997-6006.
21. (g) Liu, H.; Wang, L.; Brock, A.; Wong, C.-H.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 1702-1703.
22. (h) Miller, J. S.; Dudkin, V. Y.; Lyon, G. J.; Muir, T. W.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 431-434.
23. (i) Watt, G. M.; Lund, J.; Levens, M.; Kolli, V. S. K.; Jefferis, R.; Boons, G.-J. Chem. Biol. 2003, 10, 807-814.
24. (j) Gamblin, D. P.; Garnier, P.; van Kasteren, S.; Oldham, N. J.; Fairbanks, A. J.; Davis, B. G. Angew. Chem., Int. Ed. 2004, 43, 828-833.
25. (k) Peri, F.; Nicotra, F. Chem. Commun. 2004, 623-627.
26. (l) Warren, J. D.; Miller, J. S.; Keding, S. J.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 6576-6578.
27. (m) Zhu, X.; Schmidt, R. R. Chem. Eur. J. 2004, 10, 875-887.
28. (a) Kuijpers, B. H. M.; Groothuys, S.; Keereweer, A. B. R.; Quaedflieg, P. J. L. M.; Blaauw, R. H.; van Delft, F. L.; Rutjes, F. P. J. T. Org. Lett. 2004, 6, 3123-3126.
29. (b) Lin, H.; Walsh, C. T. J. Am. Chem. Soc. 2004, 126, 13998-14003.
30. (a) Durek, T.; Alexandrov, K.; Goody, R. S.; Hildebrand, A.; Heinemann, I.; Waldmann, H. J. Am. Chem. Soc. 2004, 126, 16368-16378.
31. (b) Kragol, G.; Lumbierres, M.; Palomo, J. M.; Waldmann, H. Angew. Chem., Int. Ed. 2004, 43, 5839-5842.
32. (a) Ghomashchi, F.; Zhang, X.; Liu, L.; Gelb, M. H. Biochemistry 1995, 34, 11910-11918.
33. (b) Koppitz, M.; Spellig, T.; Kahmann, R.; Kessler, H. Int. J. Pept. Protein Res. 1996, 48, 377-390.
34. (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
35. (b) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247-258.
36. (c) Hu, X. E. Tetrahedron 2004, 60, 2701-2743.
37. Full description of each abbreviated term is given in the Supporting Information.
38. (a) Nakajima, K.; Tanaka, T.; Morita, K.; Okawa, K. Bull Chem. Soc. Jpn. 1980, 53, 283-284.
39. (b) Okawa, K.; Nakajima, K. Biopolymers 1981, 20, 1811-1821.
40. (c) Korn, A.; Rudolph-Böhner, S.; Moroder, L. Tetrahedron 1994, 50, 1717-1730.
41. (a) Kuyl-Yeheskiely, E.; Dreef-Tromp, C. M.; van der Marel, G. A.; van Boom, J. H. Recl. Trav. Chim. Pays-Bas 1989, 108, 314-316.
42. (b) Nakajima, K.; Oda, H.; Okawa, K. Bull. Chem. Soc. Jpn. 1983, 56, 520-522.
43. (c) Kogami, Y.; Okawa, K. Bull. Chem. Soc. Jpn. 1987, 60, 2963-2965.
44. (d) Wipf, P.; Uto, Y. J. Org. Chem. 2000, 65, 1037-1049.
45. Wakamiya, T.; Shimbo, K.; Shiba, T.; Nakajima, K.; Neya, M.; Okawa, K. Bull. Chem. Soc. Jpn. 1982, 55, 3878-3881.
46. For initial report, see Galonić D. P.; van der Donk, W. A.; Gin, D. Y. J. Am. Chem. Soc. 2004, 126, 12712-12713.
47. Tanaka, T.; Nakajima, K.; Okawa, K. Bull. Chem. Soc. Jpn. 1980, 53, 1352-1355.
48. (a) Hou, X.-L.; Fan, R.-H.; Dai, L.-X. J. Org. Chem. 2002, 67, 5295-5300.
49. (b) Fan, R.-H.; Hou, X.-L. J. Org. Chem. 2003, 68, 726-730.
50. 2 amino acid adduct was obtained as a single diastereomer, which is presumably formed via inventive displacement at the aziridine α-carbon.
51. Buckler, S. A. J. Am. Chem. Soc. 1962, 84, 3093-3097.
52. tBu with benzylamine: Turner, J. J.; Sikkema, F. D.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Synlett 2001, 1727-1730.
53. The major product remained unchanged after resubjection to the reaction conditions.
54. (a) Baran, E.; Drabarek, S. Pol. J. Chem. 1978, 52, 941-946.
55. (b) Gerz, M.; Matter, H.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 269-271.
56. (c) Driguez, H. ChemBioChem 2001, 2, 311-318.
57. (d) Jahn, M.; Maries, J.; Warren, R. A. J.; Withers, S. G. Angew. Chem., Int. Ed. 2003, 42, 352-354.
58. Low conversion to the desired product was observed after prolonged reaction time when 0.1 equiv of DBU was used in this reaction.
59. A similar mode of reactivity of acylated aziridines was previously observed by Okawa in the reaction of acylated Azy-containing peptides with primary amines (ref 12a).
60. Bollhagen, R.; Schmiedberger, M.; Barlos, K.; Grell, E. J. Chem. Soc., Chem. Commun. 1994, 2559-2560.
61. Wadem J. D.; Bedford, J.; Sheppard, R. C.; Tregearm G. W. Pept. Res. 1991, 4, 194-199.
62. Shao, H.; Jiang, X.; Gantzel, P.; Goodman, M. Chem. Biol. 1994, 1, 231-234.
63. Fu, P.; Layfield, S.; Ferraro, T.; Tomiyama, H.; Hutson, J.; Otvos Jr., L.; Tregear, G. W.; Bathgate, R. A. D.; Wade, J. D. J. Peptide Res. 2004, 63, 91-98.
64. (a) Barbacid, M. Annu. Rev. Biochem. 1987, 56, 779-827.
65. (b) Bos, J. L. Cancer Res. 1989, 49, 4682-4689.
66. Reactions in entries 8-10 were carried out by heating the reaction mixture to 60 °C to allow for faster reaction. A decrease in the yields of the isolated products in these reactions may be attributed to the thermal instability of the 2-chlorotrityl linker.
67. (a) Liang, R.; Andreotti, A. H.; Kahne, D. J. Am. Chem. Soc. 1995, 117, 10395-10396.
68. (b) Live, D. H.; Williams, L. J.; Kuduk, S. D.; Schwarz, J. B.; Glunz, P. W.; Chen, X.-T.; Sames, D.; Kumar, R. A.; Danishefsky, S. J. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 3489-3493.
69. (c) Schuman, J.; Qiu, D.; Koganty, R. R.; Longenecker, B. M.; Campbell, A. P. Glycoconjugate J. 2000, 17, 835-848.
70. (d) Coltart, D. M.; Royyuru, A. K.; Williams, L. J.; Glunz, P. W.; Sames, D.; Kuduk, S. D.; Schwarz, J. B.; Chen, X.-T.; Danishefsky, S. J.; Live, D. H. J. Am. Chem. Soc. 2002, 124, 9833-9844.
71. (e) Schuman, J.; Campbell, A. P.; Koganty, R. R.; Longenecker, B. M. J. Pept. Res. 2003, 61, 91-108.
72. In these reactions, the ratio of products was determined by NMR analysis of the crude product mixture. In instances when the analysis of crude NMR data did not allow an accurate estimate of this ratio, products were analyzed by HPLC-ESI.
73. 1Bu)AlaGly pentapeptide was swelled in DMF containing 20% DMSO (v/v) and then reacted with EtSH and DBU, the same product distribution was observed.
74. A similar distribution of products was observed in the reaction of these two coupling partners in 10% DMSO in DMF (v/v) and in the presence of 2 M ethylenecarbonate in DMF.
75. A substantial decrease in the ligation rate for the peptides possessing N-alkyl amino acids in the [Azy-2] position was observed for all of the tested peptides.
76. While the expected glycosylated cysteine adduct was the major component of the crude mixture, two other minor carbohydrate-containing products were observed after cleavage from the solid support. Upon removal of O-acetates with sodium methoxide in methanol. a C3:C2 adduct ratio of 3.7:1.0 was obtained (HPLC-ESI).
77. (a) Burgess, K.; Ho, K.-K.; Pettitt, B. M. J. Am. Chem. Soc. 1994, 116, 799-800.
78. (b) Burgess, K.; Li, W.; Lim, D.; Moye-Sherman, D. Biopolymers 1997, 42, 439-453.
79. (c) Vass, E.; Hollósi, M.; Besson, F.; Buchet, R. Chem. Rev. 2003, 103, 1917-1954.
80. (d) Jiménez, A. I.; Ballano, G.; Cativiela, C. Angew. Chem., Int. Ed. 2005, 44, 396-399.
81. Narita, M.; Tomotake, Y.; Isokawa, S.; Matsuzawa, T.; Miyauchi, T. Macromolecules 1984, 17, 1903-1906.
82. Peptides 51 and 52 were prepared starting from glycine-preloaded 2-chlorotrityl polystyrene resin 21 with a loading of 0.78 mmol/g.
83. Hyde, C.; Johnson, T.; Sheppard, R. C. J. Chem. Soc., Chem. Commun. 1992, 1573-1575.
84. (a) Toniolo, C.; Bonora, G. M.; Mutter, M.; Pillai, V. N. R. Makromol. Chem. 1981, 182, 2007-2014.
85. (b) Rijkers, D. T. S.; Höppener, J. W. M.; Posthuma, G.; Lips, C. J. M.; Liskamp, R. M. J. Chem. Eur. J. 2002, 8, 4285-4291.
86. (c) Wu, C. W.; Kirshenbaurn, K.; Sanborn, T. J.; Patch, J. A.; Huang, K.; Dill, K. A.; Zuckermann, R. N.; Barron, A. E. J. Am. Chem. Soc. 2003, 125, 13525-13530.
87. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779.
88. Shin, Y.; Winans, K. A.; Backes, B. J.; Kent, S. B. H.; Ellman, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 1999, 121, 11684-11689.
89. Matsumura, S.; Takahashi, T.; Ueno, A.; Mihara, H. Chem. Eur. J. 2003, 9, 4829-4837.