One-pot hydrazide-based native chemical ligation for efficient chemical synthesis and structure determination of toxin Mambalgin-1

Chemical Communications

Volumn 50, Issue 44, 2014, Pages 5837-5839

  Pan, Man ^a,b   He, Yao ^a   Wen, Ming ^a   Wu, Fangming ^a   Sun, Demeng ^a,b   Li, Sijian ^c   Zhang, Longhua ^a   Li, Yiming ^b,c   Tian, Changlin ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b TSINGHUA UNIVERSITY   (China)

^c HEFEI UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACID SENSING ION CHANNEL; ASIC1 PROTEIN, HUMAN; AZIDE; MAMBALGIN-1, DENDROASPIS POLYLEPIS; PEPTIDE; SNAKE VENOM; ACID SENSING ION CHANNEL 1A; CYSTEINE; DISULFIDE; GLUTATHIONE; HYDRAZIDE; MAMBALGIN 1; POLYPEPTIDE; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; NUCLEAR MAGNETIC RESONANCE; PROTEIN CONFORMATION; SYNTHESIS; AMINO TERMINAL SEQUENCE; ANIMAL CELL; ARTICLE; AZIDE SWITCH METHOD; CHO CELL LINE; COS 7 CELL LINE; ELECTROPHYSIOLOGY; FEMALE; HYDRAZIDE BASED NATIVE CHEMICAL LIGATION; IN VITRO STUDY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ONE POT SYNTHESIS; PATCH CLAMP TECHNIQUE; PH; PROTEIN FOLDING; PROTEIN PURIFICATION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; RACEMIZATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; TOXIN STRUCTURE; TOXIN SYNTHESIS;

ACID SENSING ION CHANNELS; AZIDES; ELAPID VENOMS; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES; PROTEIN CONFORMATION;

EID: 84899846744     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc00779d     Document Type: Article

References (37)

1. A. Baron, S. Diochot, M. Salinas, E. Deval, J. Noël, E. Lingueglia, Toxicon, 2013, 75, 187-204
2. R. J. P. Dawson, J. Benz, P. Stohler, T. Tetaz, C. Joseph, S. Huber, G. Schmid, D. Hugin, P. Pflimlin, G. Trube, M. G. Rudolph, M. Hennig, A. Ruf, Nat. Commun., 2012, 3, 936-944
3. I. Baconguis, E. Gouaux, Nature, 2012, 489, 400-405
4. S. Diochot, A. Baron, M. Salinas, D. Douguet, S. Scarzello, A.-S. Dabert-Gay, D. Debayle, V. Friend, A. Alloui, M. Lazdunski, E. Lingueglia, Nature, 2012, 490, 552-555
5. D. J. Craik, C. I. Schroeder, Angew. Chem., Int. Ed., 2013, 52, 3071-3073
6. A. Ghassemian, C. I. A. Wang, M. K. Yau, R. C. Reid, R. J. Lewis, D. P. Fairlie, P. F. Alewood, D. J. Craik, T. Durek, Chem. Commun., 2013, 49, 2356-2358
7. J. E. Jensen, T. Durek, P. F. Alewood, D. J. Adams, G. F. King, L. D. Rash, Toxicon, 2009, 54, 56-61
8. T. Durek, I. Vetter, C. I. A. Wang, L. Motin, O. Knapp, D. J. Adams, R. J. Lewis, P. F. Alewood, ACS Chem. Biol., 2013, 8, 1215-1222
9. R. J. Clark, J. Jensen, S. T. Nevin, B. P. Callaghan, D. J. Adams, D. J. Craik, Angew. Chem., Int. Ed., 2010, 49, 6545-6548
10. D. Bang, D. S. B. H. Kent, Angew. Chem., Int. Ed., 2004, 43, 2534-2538
11. D. Bang, B. L. Pentelute, S. B. H. Kent, Angew. Chem., Int. Ed., 2006, 45, 3985
12. J. S. Zheng, H. K. Cui, G. M. Fang, W. X. Xi, L. Liu, ChemBioChem, 2010, 11, 511-515
13. R. A. Morales, N. L. Daly, I. Vetter, M. Mobli, I. A. Napier, D. J. Craik, R. J. Lewis, M. J. Christie, G. F. King, P. F. Alewood, T. Durek, ChemBioChem, 2010, 11, 1882-1888
14. C. I. Schroeder, L. D. Rash, X. Vila-Farrs, K. J. Rosengren, M. Mobli, G. F. King, P. F. Alewood, D. J. Craik, T. Durek, Angew. Chem., Int. Ed., 2014, 53, 1017-1020
15. S. B. H. Kent, Chem. Soc. Rev., 2009, 38, 338
16. V. R. Pattabiraman, J. W. Bode, Nature, 2011, 480, 471
17. L. Raibaut, N. Ollivier, O. Melnyk, Chem. Soc. Rev., 2012, 41, 7001
18. P. Siman, A. Brik, Org. Biomol. Chem., 2012, 10, 5684-5697
19. P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. H. Kent, Science, 1994, 266, 776-779
20. L. E. Canne, S. J. Bark, S. B. H. Kent, J. Am. Chem. Soc., 1996, 111, 5891-5896
21. V. Y. Torbeev, S. B. H. Kent, Angew. Chem., Int. Ed., 2007, 46, 1667-1670
22. K. S. A. Kumar, S. N. Bavikar, L. Spasser, T. Moyal, S. Ohayon, A. Brik, Angew. Chem., Int. Ed., 2011, 50, 6137-6141
23. S. Liu, B. L. Pentelute, S. B. H. Kent, Angew. Chem., Int. Ed., 2012, 51, 993-999
24. M. Avital-Shmilovici, K. Mandal, Z. P. Gates, N. B. Phillips, M. A. Weiss, S. B. H. Kent, J. Am. Chem. Soc., 2013, 135, 3173-3185
25. Y. C. Huang, Y. M. Li, Y. Chen, M. Pan, Y. T. Li, L. Yu, Q. X. Guo, L. Liu, Angew. Chem., Int. Ed., 2013, 52, 4858-4862
26. J. S. Zheng, S. Tang, Y. C. Huang, L. Liu, Acc. Chem. Res., 2013, 46, 2475-2484
27. G. M. Fang, Y. M. Li, F. Shen, Y. C. Huang, J. B. Li, Y. Lin, H. K. Cui, L. Liu, Angew. Chem., Int. Ed., 2011, 50, 7645-7649
28. J. S. Zheng, H. N. Chang, F. L. Wang, L. Liu, J. Am. Chem. Soc., 2011, 133, 11080-11083
29. Y. M. Li, M. Y. Yang, Y. C. Huang, Y. T. Li, P. R. Chen, L. Liu, ACS Chem. Biol., 2012, 7, 1015-1022
30. G. M. Fang, J. X. Wang, L. Liu, Angew. Chem., Int. Ed., 2012, 51, 10347-10350
31. J. S. Zheng, S. Tang, Y. K. Qi, Z. P. Wang, L. Liu, Nat. Protoc., 2013, 8, 2483-2495
32. P. Siman, S. V. Karthikeyan, M. Nikolov, W. Fischle, A. Brik, Angew. Chem., Int. Ed., 2013, 52, 8059
33. Y. M. Li, Y. T. Li, M. Pan, X. Q. Kong, Y. C. Huang, Z. Y. Hong, L. Liu, Angew. Chem., Int. Ed., 2014, 53, 2198-2202
34. N. Nepomniaschiy, V. Grimminger, A. Cohen, S. DiGiovanni, H. A. Lashuel, A. Brik, Org. Lett., 2008, 10, 5243-5246
35. S. D. Santos, A. Chandravarkar, B. Mandal, R. Mimna, K. Murat, L. Saucede, P. Tella, G. Tuchscherer, M. Mutter, J. Am. Chem. Soc., 2005, 127, 11888-11889
36. A. Taniguchi, Y. Sohma, M. Kimura, T. Okada, K. Ikeda, Y. Hayashi, T. Kimura, S. Hirota, K. Matsuzaki, Y. Kiso, J. Am. Chem. Soc., 2005, 128, 696-699
37. K. Wuthrich, NMR of proteins and nucleic acids, 1986, Wiley, New York