SCOPUS 정보 검색 플랫폼

Tetrahedron

Volumn 69, Issue 12, 2013, Pages 2555-2559

Total synthesis of α-conotoxin MII using a soluble-tag-assisted method

(5) Kitada, Shingo a Fujita, Shuji b Okada, Yohei a Kim, Shokaku a Chiba, Kazuhiro a

a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY (Japan)

b Research and Development Division (Japan)

Author keywords

Conotoxin MII; Disulfide bond; Hydrophobic benzyl amine; Liquid phase peptide synthesis; Soluble tag

Indexed keywords

ALPHA CONOTOXIN MII; AMINO ACID; CYSTEINE; IODINE; MONOMETHOXYTRITYL; TRITYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DISULFIDE BOND; OXIDATION; PRIORITY JOURNAL; PROTEIN FOLDING; SYNTHESIS;

EID: 84874110568 PISSN: 00404020 EISSN: 14645416 Source Type: Journal
DOI: 10.1016/j.tet.2013.01.068 Document Type: Article

Times cited : (23)

References (60)

1
- 0347989461
- H. Terlau, and B.M. Olivera Physiol. Rev. 84 2004 41 68
- (2004) Physiol. Rev. , vol.84 , pp. 41-68
- Terlau, H.¹ Olivera, B.M.²

2
- 84856508426
- B.B. Carstens, R.J. Clark, N.L. Daly, P.J. Harvey, Q. Kaas, and D.J. Craik Curr. Pharm. Des. 17 2011 4242 4253
- (2011) Curr. Pharm. Des. , vol.17 , pp. 4242-4253
- Carstens, B.B.¹ Clark, R.J.² Daly, N.L.³ Harvey, P.J.⁴ Kaas, Q.⁵ Craik, D.J.⁶

3
- 67649592405
- R. Halai, and D.J. Craik Nat. Prod. Rep. 26 2009 526 536
- (2009) Nat. Prod. Rep. , vol.26 , pp. 526-536
- Halai, R.¹ Craik, D.J.²

4
- 34548643963
- D.J. Craik, and D.J. Adams ACS Chem. Biol. 2 2007 457 468
- (2007) ACS Chem. Biol. , vol.2 , pp. 457-468
- Craik, D.J.¹ Adams, D.J.²

5
- 0037474213
- A. Nicke, M.L. Loughnan, E.L. Millard, P.F. Alewood, D.J. Adams, N.L. Daly, D.J. Craik, and R.J. Lewis J. Biol. Chem. 278 2003 3137 3144
- (2003) J. Biol. Chem. , vol.278 , pp. 3137-3144
- Nicke, A.¹ Loughnan, M.L.² Millard, E.L.³ Alewood, P.F.⁴ Adams, D.J.⁵ Daly, N.L.⁶ Craik, D.J.⁷ Lewis, R.J.⁸

6
- 67649133580
- L. Azam, and J.M. McIntosh Acta Pharmacol. Sin. 30 2009 771 783
- (2009) Acta Pharmacol. Sin. , vol.30 , pp. 771-783
- Azam, L.¹ McIntosh, J.M.²

7
- 11144331404
- M. Ellison, F. Gao, H.-L. Wang, S.M. Sine, J.M. McIntosh, and B.M. Olivera Biochemistry 43 2004 16019 16026
- (2004) Biochemistry , vol.43 , pp. 16019-16026
- Ellison, M.¹ Gao, F.² Wang, H.-L.³ Sine, S.M.⁴ McIntosh, J.M.⁵ Olivera, B.M.⁶

8
- 0035033785
- J.L. Dutton, and D.J. Craik Curr. Med. Chem. 8 2001 327 344
- (2001) Curr. Med. Chem. , vol.8 , pp. 327-344
- Dutton, J.L.¹ Craik, D.J.²

9
- 0031026798
- S.C. Harvey, J.M. McIntosh, G.E. Cartier, F.N. Maddox, and C.W. Luetje Mol. Pharmacol. 51 1997 336 342
- (1997) Mol. Pharmacol. , vol.51 , pp. 336-342
- Harvey, S.C.¹ McIntosh, J.M.² Cartier, G.E.³ Maddox, F.N.⁴ Luetje, C.W.⁵

10
- 0029871748
- G.E. Cartier, D. Yoshikami, W.R. Gray, S. Luo, B.M. Olivera, and J.M. McIntosh J. Biol. Chem. 271 1996 7522 7528
- (1996) J. Biol. Chem. , vol.271 , pp. 7522-7528
- Cartier, G.E.¹ Yoshikami, D.² Gray, W.R.³ Luo, S.⁴ Olivera, B.M.⁵ McIntosh, J.M.⁶

11
- 0028981913
- D.S. Johnson, J. Martinez, A.B. Elgoyhen, S.F. Heinemann, and J.M. McIntosh Mol. Pharmacol. 48 1995 194 199
- (1995) Mol. Pharmacol. , vol.48 , pp. 194-199
- Johnson, D.S.¹ Martinez, J.² Elgoyhen, A.B.³ Heinemann, S.F.⁴ McIntosh, J.M.⁵

12
- 0028361574
- J.M. McIntosh, D. Yoshikami, E. Mahe, D.B. Nielsen, J.E. Rivier, W.R. Gray, and B.M. Olivera J. Biol. Chem. 269 1994 16733 16739
- (1994) J. Biol. Chem. , vol.269 , pp. 16733-16739
- McIntosh, J.M.¹ Yoshikami, D.² Mahe, E.³ Nielsen, D.B.⁴ Rivier, J.E.⁵ Gray, W.R.⁶ Olivera, B.M.⁷

13
- 84861666297
- R. Yu, Q. Kaas, J. David, and D.J. Craik J. Phys. Chem. B 116 2012 6097 6105
- (2012) J. Phys. Chem. B , vol.116 , pp. 6097-6105
- Yu, R.¹ Kaas, Q.² David, J.³ Craik, D.J.⁴

14
- 79953658296
- R. Yu, D.J. Craik, and Q. Kaas PLoS Comput. Biol. 7 2011 e1002011
- (2011) PLoS Comput. Biol. , vol.7 , pp. 1002011
- Yu, R.¹ Craik, D.J.² Kaas, Q.³

15
- 66149116389
- C. Armishaw, A.A. Jensen, T. Balle, R.J. Clark, K. Harpsøe, C. Skonberg, T. Liljefors, and K. Strømgaard J. Biol. Chem. 284 2009 9498 9512
- (2009) J. Biol. Chem. , vol.284 , pp. 9498-9512
- Armishaw, C.¹ Jensen, A.A.² Balle, T.³ Clark, R.J.⁴ Harpsøe, K.⁵ Skonberg, C.⁶ Liljefors, T.⁷ Strømgaard, K.⁸

16
- 0033067115
- I.V. Maslennikov, Z.O. Shenkarev, M.N. Zhmak, V.T. Ivanov, C. Methfessel, V.I. Tsetlin, and A.S. Arseniev FEBS Lett. 444 1999 275 280
- (1999) FEBS Lett. , vol.444 , pp. 275-280
- Maslennikov, I.V.¹ Shenkarev, Z.O.² Zhmak, M.N.³ Ivanov, V.T.⁴ Methfessel, C.⁵ Tsetlin, V.I.⁶ Arseniev, A.S.⁷

17
- 0033168019
- J. Gehrmann, N.L. Daly, P.F. Alewood, and D.J. Craik J. Med. Chem. 42 1999 2364 2372
- (1999) J. Med. Chem. , vol.42 , pp. 2364-2372
- Gehrmann, J.¹ Daly, N.L.² Alewood, P.F.³ Craik, D.J.⁴

18
- 0040017648
- J.P. Rogers, P. Luginbühl, G.S. Shen, R.T. McCabe, R.C. Stevens, and D.E. Wemmer Biochemistry 38 1999 3874 3882
- (1999) Biochemistry , vol.38 , pp. 3874-3882
- Rogers, J.P.¹ Luginbühl, P.² Shen, G.S.³ McCabe, R.T.⁴ Stevens, R.C.⁵ Wemmer, D.E.⁶

19
- 0033538459
- P.A. Quiram, J.J. Jones, and S.M. Sine J. Biol. Chem. 274 1999 19517 19524
- (1999) J. Biol. Chem. , vol.274 , pp. 19517-19524
- Quiram, P.A.¹ Jones, J.J.² Sine, S.M.³

20
- 0033013141
- H. Lamthanh, C. Jegou-Matheron, D. Servent, A. Ménez, and J.M. Lancelin FEBS Lett. 454 1999 293 298
- (1999) FEBS Lett. , vol.454 , pp. 293-298
- Lamthanh, H.¹ Jegou-Matheron, C.² Servent, D.³ Ménez, A.⁴ Lancelin, J.M.⁵

21
- 0032080235
- P.A. Quiram, and S.M. Sine J. Biol. Chem. 273 1998 11007 11011
- (1998) J. Biol. Chem. , vol.273 , pp. 11007-11011
- Quiram, P.A.¹ Sine, S.M.²

22
- 79959935844
- A.D. de Araujo, B. Callaghan, S.T. Nevin, N.L. Daly, D.J. Craik, M. Moretta, G. Hopping, M.J. Christie, D.J. Adams, and P.F. Alewood Angew. Chem., Int. Ed. 50 2011 6527 6529
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 6527-6529
- De Araujo, A.D.¹ Callaghan, B.² Nevin, S.T.³ Daly, N.L.⁴ Craik, D.J.⁵ Moretta, M.⁶ Hopping, G.⁷ Christie, M.J.⁸ Adams, D.J.⁹ Alewood, P.F.¹⁰

23
- 77949391358
- M. Muttenthaler, S.T. Nevin, A.A. Grishin, S.T. Ngo, P.T. Choy, N.L. Daly, S.H. Hu, C.J. Armishaw, C.I. Wang, R.J. Lewis, J.L. Martin, P.G. Noakes, D.J. Craik, D.J. Adams, and P.F. Alewood J. Am. Chem. Soc. 132 2010 3514 3522
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 3514-3522
- Muttenthaler, M.¹ Nevin, S.T.² Grishin, A.A.³ Ngo, S.T.⁴ Choy, P.T.⁵ Daly, N.L.⁶ Hu, S.H.⁷ Armishaw, C.J.⁸ Wang, C.I.⁹ Lewis, R.J.¹⁰ Martin, J.L.¹¹ Noakes, P.G.¹² Craik, D.J.¹³ Adams, D.J.¹⁴ Alewood, P.F.¹⁵

24
- 77953010796
- C.J. Armishaw, J.L. Dutton, D.J. Craik, and P.F. Alewood Biopolymers 94 2010 307 313
- (2010) Biopolymers , vol.94 , pp. 307-313
- Armishaw, C.J.¹ Dutton, J.L.² Craik, D.J.³ Alewood, P.F.⁴

25
- 61449163172
- C.A. MacRaild, J. Illesinghe, B.J. van Lierop, A.L. Townsend, M. Chebib, B.G. Livett, A.J. Robinson, and R.S. Norton J. Med. Chem. 52 2009 755 762
- (2009) J. Med. Chem. , vol.52 , pp. 755-762
- MacRaild, C.A.¹ Illesinghe, J.² Van Lierop, B.J.³ Townsend, A.L.⁴ Chebib, M.⁵ Livett, B.G.⁶ Robinson, A.J.⁷ Norton, R.S.⁸

26
- 61949466107
- A. Walewska, M. Zhang, J.J. Skalicky, D. Yoshikami, B.M. Olivera, and G. Bulaj Angew.Chem., Int. Ed. 48 2009 2221 2224
- (2009) Angew.Chem., Int. Ed. , vol.48 , pp. 2221-2224
- Walewska, A.¹ Zhang, M.² Skalicky, J.J.³ Yoshikami, D.⁴ Olivera, B.M.⁵ Bulaj, G.⁶

27
- 60149105961
- A.S. Galanis, F. Albericio, and M. Grotli Biopolymers 92 2009 23 34
- (2009) Biopolymers , vol.92 , pp. 23-34
- Galanis, A.S.¹ Albericio, F.² Grotli, M.³

28
- 44249110008
- P. Whiteaker, M.J. Marks, S. Christensen, C. Dowell, A.C. Collins, and J.M. McIntosh J. Pharmacol. Exp. Ther. 325 2008 910 919
- (2008) J. Pharmacol. Exp. Ther. , vol.325 , pp. 910-919
- Whiteaker, P.¹ Marks, M.J.² Christensen, S.³ Dowell, C.⁴ Collins, A.C.⁵ McIntosh, J.M.⁶

29
- 33744918558
- C.J. Armishaw, N.L. Daly, S.T. Nevin, D.J. Adams, D.J. Craik, and P.F. Alewood J. Biol. Chem. 281 2006 14136 14143
- (2006) J. Biol. Chem. , vol.281 , pp. 14136-14143
- Armishaw, C.J.¹ Daly, N.L.² Nevin, S.T.³ Adams, D.J.⁴ Craik, D.J.⁵ Alewood, P.F.⁶

30
- 33845197219
- V.A. Vishwanath, and J.M. McIntosh Bioconjugate Chem. 17 2006 1612 1617
- (2006) Bioconjugate Chem. , vol.17 , pp. 1612-1617
- Vishwanath, V.A.¹ McIntosh, J.M.²

31
- 33747372837
- R.J. Clark, H. Fischer, S.T. Nevin, D.J. Adams, and D.J. Craik J. Biol. Chem. 281 2006 23254 23263
- (2006) J. Biol. Chem. , vol.281 , pp. 23254-23263
- Clark, R.J.¹ Fischer, H.² Nevin, S.T.³ Adams, D.J.⁴ Craik, D.J.⁵

32
- 0001789083
- M.N. Shemyakin, Y.A. Ovchinnikov, A.A. Kiryushkin, and I.V. Kozhevnikovd Tetrahedron Lett. 6 1965 2323 2327
- (1965) Tetrahedron Lett. , vol.6 , pp. 2323-2327
- Shemyakin, M.N.¹ Ovchinnikov, Y.A.² Kiryushkin, A.A.³ Kozhevnikovd, I.V.⁴

33
- 0019703437
- K. Geckeler, V.N.R. Pillai, and M. Mutter Adv. Polym. Sci. 39 1981 65 94
- (1981) Adv. Polym. Sci. , vol.39 , pp. 65-94
- Geckeler, K.¹ Pillai, V.N.R.² Mutter, M.³

34
- 0008284919
- M. Narita, M. Hirata, K. Kusano, S. Itsuno, M. Ue, and M. Okawara Pept. Chem. 17 1980 107 112
- (1980) Pept. Chem. , vol.17 , pp. 107-112
- Narita, M.¹ Hirata, M.² Kusano, K.³ Itsuno, S.⁴ Ue, M.⁵ Okawara, M.⁶

35
- 0015151548
- M. Mutter, H. Hagenmaier, and E. Bayer Angew. Chem., Int. Ed. Engl. 10 1971 811 812
- (1971) Angew. Chem., Int. Ed. Engl. , vol.10 , pp. 811-812
- Mutter, M.¹ Hagenmaier, H.² Bayer, E.³

36
- 0015529625
- E. Bayer, and M. Mutter Nature 237 1972 512 513
- (1972) Nature , vol.237 , pp. 512-513
- Bayer, E.¹ Mutter, M.²

37
- 0026029284
- E. Bayer Angew. Chem., Int. Ed. Engl. 30 1991 113 129
- (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 113-129
- Bayer, E.¹

38
- 0031098534
- D.J. Gravert, and K.D. Janda Chem. Rev. 97 1997 489 510
- (1997) Chem. Rev. , vol.97 , pp. 489-510
- Gravert, D.J.¹ Janda, K.D.²

39
- 0036811238
- T.J. Dickerson, N.N. Reed, and K.D. Janda Chem. Rev. 102 2002 3325 3344
- (2002) Chem. Rev. , vol.102 , pp. 3325-3344
- Dickerson, T.J.¹ Reed, N.N.² Janda, K.D.³

40
- 0036811241
- D.E. Bergbreiter Chem. Rev. 102 2002 3345 3384
- (2002) Chem. Rev. , vol.102 , pp. 3345-3384
- Bergbreiter, D.E.¹

41
- 65249131079
- D.E. Bergbreiter, J. Tian, and C. Hongfa Chem. Rev. 109 2009 530 582
- (2009) Chem. Rev. , vol.109 , pp. 530-582
- Bergbreiter, D.E.¹ Tian, J.² Hongfa, C.³

42
- 0023946335
- M.M. Palcic, L.D. Heerze, M. Pierce, and O. Hindsgaul Glycoconjugate J. 5 1988 49 63
- (1988) Glycoconjugate J. , vol.5 , pp. 49-63
- Palcic, M.M.¹ Heerze, L.D.² Pierce, M.³ Hindsgaul, O.⁴

43
- 0028881538
- P. Stangier, M.M. Palcic, and D.R. Bundle Carbohydr. Res. 267 1995 153 159
- (1995) Carbohydr. Res. , vol.267 , pp. 153-159
- Stangier, P.¹ Palcic, M.M.² Bundle, D.R.³

44
- 33751134981
- O. Kanie, F. Barresi, Y.L. Ding, J. Labbe, A. Otter, L.S. Forsberg, B. Ernst, and O. Hindsgaul Angew. Chem., Int. Ed. 34 1996 2720 2722
- (1996) Angew. Chem., Int. Ed. , vol.34 , pp. 2720-2722
- Kanie, O.¹ Barresi, F.² Ding, Y.L.³ Labbe, J.⁴ Otter, A.⁵ Forsberg, L.S.⁶ Ernst, B.⁷ Hindsgaul, O.⁸

45
- 0029895067
- Y. Ding, J. Labbe, O. Kanie, and O. Hindsgaul Bioorg. Med. Chem. 4 1996 683 692
- (1996) Bioorg. Med. Chem. , vol.4 , pp. 683-692
- Ding, Y.¹ Labbe, J.² Kanie, O.³ Hindsgaul, O.⁴

46
- 0034648070
- U.J. Nilsson J. Chromatogr., A 885 2000 305 319
- (2000) J. Chromatogr., A , vol.885 , pp. 305-319
- Nilsson, U.J.¹

47
- 0032168143
- U.J. Nilsson, E.J.L. Fournier, and O. Hindsgaul Bioorg. Med. Chem. 6 1998 1563 1575
- (1998) Bioorg. Med. Chem. , vol.6 , pp. 1563-1575
- Nilsson, U.J.¹ Fournier, E.J.L.² Hindsgaul, O.³

48
- 27744464995
- R. Sato, K. Toma, K. Nomura, M. Takagi, T. Yoshida, Y. Azefu, and H. Tamiaki J. Carbohydr. Chem. 23 2004 375 388
- (2004) J. Carbohydr. Chem. , vol.23 , pp. 375-388
- Sato, R.¹ Toma, K.² Nomura, K.³ Takagi, M.⁴ Yoshida, T.⁵ Azefu, Y.⁶ Tamiaki, H.⁷

49
- 33746265839
- O. Kanie, I. Ohtsuka, T. Ako, S. Daikoku, Y. Kame, and R. Kato Angew. Chem., Int. Ed. 45 2006 3851 3854
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 3851-3854
- Kanie, O.¹ Ohtsuka, I.² Ako, T.³ Daikoku, S.⁴ Kame, Y.⁵ Kato, R.⁶

50
- 0033549672
- V. Pozsgay Org. Lett. 1 1999 477 479
- (1999) Org. Lett. , vol.1 , pp. 477-479
- Pozsgay, V.¹

51
- 0033996771
- V. Pozsgay Tetrahedron: Asymmetry 11 2000 151 172
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 151-172
- Pozsgay, V.¹

52
- 19744374836
- J. Bauer, and J. Rademann J. Am. Chem. Soc. 127 2005 7296 7297
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 7296-7297
- Bauer, J.¹ Rademann, J.²

53
- 66149106187
- L. Encinas, and J.L. Chiara Eur. J. Org. Chem. 2009 2163 2173
- (2009) Eur. J. Org. Chem. , pp. 2163-2173
- Encinas, L.¹ Chiara, J.L.²

54
- 27944482555
- J. Li, S. Sung, J. Tian, and D.E. Bergbreiter Tetrahedron 61 2005 12081 12092
- (2005) Tetrahedron , vol.61 , pp. 12081-12092
- Li, J.¹ Sung, S.² Tian, J.³ Bergbreiter, D.E.⁴

55
- 84862190826
- J. Guo, Y.-J. Lu, L. Zhang, and X.-S. Ye Synlett 2012 1696 1700
- (2012) Synlett , pp. 1696-1700
- Guo, J.¹ Lu, Y.-J.² Zhang, L.³ Ye, X.-S.⁴

56
- 0036061371
- K. Chiba, Y. Kono, S. Kim, K. Nishimoto, Y. Kitano, and M. Tada Chem. Commun. 2002 1766 1767
- (2002) Chem. Commun. , pp. 1766-1767
- Chiba, K.¹ Kono, Y.² Kim, S.³ Nishimoto, K.⁴ Kitano, Y.⁵ Tada, M.⁶

57
- 41549107085
- S. Kim, A. Tsuruyama, A. Ohmori, and K. Chiba Chem. Commun. 2008 1816 1818
- (2008) Chem. Commun. , pp. 1816-1818
- Kim, S.¹ Tsuruyama, A.² Ohmori, A.³ Chiba, K.⁴

58
- 70349910271
- M. Iijima, Y. Mikami, T. Yoshioka, S. Kim, H. Kamiya, and K. Chiba Langmuir 25 2009 11043 11047
- (2009) Langmuir , vol.25 , pp. 11043-11047
- Iijima, M.¹ Mikami, Y.² Yoshioka, T.³ Kim, S.⁴ Kamiya, H.⁵ Chiba, K.⁶

59
- 77958513278
- G. Tana, S. Kitada, S. Fujita, Y. Okada, S. Kim, and K. Chiba Chem. Commun. 2010 8219 8221
- (2010) Chem. Commun. , pp. 8219-8221
- Tana, G.¹ Kitada, S.² Fujita, S.³ Okada, Y.⁴ Kim, S.⁵ Chiba, K.⁶

60
- 79960345833
- S. Kitada, S. Fujita, Y. Okada, S. Kim, and K. Chiba Bioorg. Med. Chem. Lett. 21 2011 4476 4479
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 4476-4479
- Kitada, S.¹ Fujita, S.² Okada, Y.³ Kim, S.⁴ Chiba, K.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.