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Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 15, 2011, Pages 4476-4479

Hydrophobic tag-assisted liquid-phase synthesis of a growth hormone-inhibiting peptide somatostatin

(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

Cyclic peptide; Disulfide bond; Hydrophobic tag; Liquid phase peptide synthesis; Somatostatin

Indexed keywords

SOMATOSTATIN;

ARTICLE; CONCENTRATION (PARAMETERS); DISULFIDE BOND; DRUG SYNTHESIS; PROTEIN MODIFICATION;

AMINO ACID SEQUENCE; DISULFIDES; HUMAN GROWTH HORMONE; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; OXIDATION-REDUCTION; SOMATOSTATIN;

EID: 79960345833 PISSN: 0960894X EISSN: 14643405 Source Type: Journal
DOI: 10.1016/j.bmcl.2011.06.004 Document Type: Article

Times cited : (35)

References (55)

1
- 77954549222
- K. Sasaki, and D. Crich Org. Lett. 12 2010 3254
- (2010) Org. Lett. , vol.12 , pp. 3254
- Sasaki, K.¹ Crich, D.²

2
- 70449365102
- Y. Li, A. Yongye, M. Giulianotti, K. Martinez-Mayorga, Y. Yu, A. Richard, and R.A. Houghten J. Comb. Chem. 11 2009 1066
- (2009) J. Comb. Chem. , vol.11 , pp. 1066
- Li, Y.¹ Yongye, A.² Giulianotti, M.³ Martinez-Mayorga, K.⁴ Yu, Y.⁵ Richard, A.⁶ Houghten, R.A.⁷

3
- 43549104559
- T. Doi, S. Kamioka, S. Shimazu, and T. Takahashi Org. Lett. 10 2008 817
- (2008) Org. Lett. , vol.10 , pp. 817
- Doi, T.¹ Kamioka, S.² Shimazu, S.³ Takahashi, T.⁴

4
- 34347205269
- Q. Xiao, and D. Pei J. Med. Chem. 50 2007 3132
- (2007) J. Med. Chem. , vol.50 , pp. 3132
- Xiao, Q.¹ Pei, D.²

5
- 77950402397
- R. Hili, V. Rai, and K.A.K. Yudin J. Am. Chem. Soc. 132 2010 2889
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 2889
- Hili, R.¹ Rai, V.² Yudin, K.A.K.³

6
- 36849088097
- R.A. Turner, A.G. Oliver, and R.R.S. Lokey Org. Lett. 9 2007 5011
- (2007) Org. Lett. , vol.9 , pp. 5011
- Turner, R.A.¹ Oliver, A.G.² Lokey, R.R.S.³

7
- 33845962046
- F. Kopp, C. Mahlert, J. Grünewald, and M.A. Marahiel J. Am. Chem. Soc. 128 2006 16478
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 16478
- Kopp, F.¹ Mahlert, C.² Grünewald, J.³ Marahiel, M.A.⁴

8
- 77957324874
- T. Yoshiya, H. Kawashima, Y. Hasegawa, K. Okamoto, T. Kimura, Y. Sohma, and Y. Kiso J. Pept. Sci. 16 2010 437
- (2010) J. Pept. Sci. , vol.16 , pp. 437
- Yoshiya, T.¹ Kawashima, H.² Hasegawa, Y.³ Okamoto, K.⁴ Kimura, T.⁵ Sohma, Y.⁶ Kiso, Y.⁷

9
- 47249083936
- M. Čemažar, and D.J. Craik J. Pept. Sci. 14 2008 683
- (2008) J. Pept. Sci. , vol.14 , pp. 683
- Čemažar, M.¹ Craik, D.J.²

10
- 34250648543
- A. Montero, F. Albericio, M. Royo, and B. Herradón Chem. Eur. J. 2007 2007 1301
- (2007) Chem. Eur. J. , vol.2007 , pp. 1301
- Montero, A.¹ Albericio, F.² Royo, M.³ Herradón, B.⁴

11
- 16244421381
- D. Flora, H. Mo, J.P. Mayer, M.A. Khan, and L.Z. Yan Bioorg. Med. Chem. Lett. 15 2005 1065
- (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 1065
- Flora, D.¹ Mo, H.² Mayer, J.P.³ Khan, M.A.⁴ Yan, L.Z.⁵

12
- 78449304271
- B.B. Metaferia, M. Rittler, J.S. Gheeya, A. Lee, H. Hempel, A. Plaza, W.G. Stetler-Stevenson, C.A. Bewley, and J. Khan Bioorg. Med. Chem. Lett. 20 2010 7337
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 7337
- Metaferia, B.B.¹ Rittler, M.² Gheeya, J.S.³ Lee, A.⁴ Hempel, H.⁵ Plaza, A.⁶ Stetler-Stevenson, W.G.⁷ Bewley, C.A.⁸ Khan, J.⁹

13
- 28044451331
- A. Mollica, P. Davis, S.-W. Ma, F. Porreca, J. Lai, and V.J. Hruby Bioorg. Med. Chem. Lett. 16 2006 367
- (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 367
- Mollica, A.¹ Davis, P.² Ma, S.-W.³ Porreca, F.⁴ Lai, J.⁵ Hruby, V.J.⁶

14
- 0346392250
- L.Z. Yan, P. Edwards, D. Flora, and J.P. Mayer Tetrahedron Lett. 45 2004 923
- (2004) Tetrahedron Lett. , vol.45 , pp. 923
- Yan, L.Z.¹ Edwards, P.² Flora, D.³ Mayer, J.P.⁴

15
- 0000698830
- T. Eichler, and R.A. Houghten Protein Pept. Lett. 4 1997 157
- (1997) Protein Pept. Lett. , vol.4 , pp. 157
- Eichler, T.¹ Houghten, R.A.²

16
- 53049095529
- S. Kamioka, S. Shimazu, T. Doi, and T. Takahashi J. Comb. Chem. 10 2008 681
- (2008) J. Comb. Chem. , vol.10 , pp. 681
- Kamioka, S.¹ Shimazu, S.² Doi, T.³ Takahashi, T.⁴

17
- 31544445036
- K. Nagai, T. Doi, T. Sekiguchi, I. Namatame, T. Sunazuka, H. Tomoda, S. mura, and T. Takahashi J. Comb. Chem. 8 2006 103
- (2006) J. Comb. Chem. , vol.8 , pp. 103
- Nagai, K.¹ Doi, T.² Sekiguchi, T.³ Namatame, I.⁴ Sunazuka, T.⁵ Tomoda, H.⁶ Mura, S.⁷ Takahashi, T.⁸

18
- 0027703505
- M.R. Ghadiri, J.R. Granja, R.A. Milligan, D.E. McRee, and N. Khazanovich Nature 366 1993 324
- (1993) Nature , vol.366 , pp. 324
- Ghadiri, M.R.¹ Granja, J.R.² Milligan, R.A.³ McRee, D.E.⁴ Khazanovich, N.⁵

19
- 4344679634
- K. Kelly, H. Alencar, M. Funovics, U. Mahmood, and R. Weissleder Cancer Res. 64 2004 6247
- (2004) Cancer Res. , vol.64 , pp. 6247
- Kelly, K.¹ Alencar, H.² Funovics, M.³ Mahmood, U.⁴ Weissleder, R.⁵

20
- 33645077862
- D.J. Craik Science 311 2006 1563
- (2006) Science , vol.311 , pp. 1563
- Craik, D.J.¹

21
- 33644644973
- T. Rezai, B. Yu, G.L. Millhauser, M.P. Jacobson, and R.S. Lokey J. Am. Chem. Soc. 128 2006 2510
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 2510
- Rezai, T.¹ Yu, B.² Millhauser, G.L.³ Jacobson, M.P.⁴ Lokey, R.S.⁵

22
- 67650684255
- M.A. Hossain, A. Belgi, F. Lin, S. Zhang, F. Shabanpoor, L. Chan, C. Belyea, H.-T. Truong, A.R. Blair, S. Andrikopoulos, G.W. Tregear, and J.D. Wade Bioconjug. Chem. 20 2009 1390
- (2009) Bioconjug. Chem. , vol.20 , pp. 1390
- Hossain, M.A.¹ Belgi, A.² Lin, F.³ Zhang, S.⁴ Shabanpoor, F.⁵ Chan, L.⁶ Belyea, C.⁷ Truong, H.-T.⁸ Blair, A.R.⁹ Andrikopoulos, S.¹⁰ Tregear, G.W.¹¹ Wade, J.D.¹²

23
- 34247891594
- J. Tulla-Puche, N. Bayó-Puxan, J.A. Moreno, A.M. Francesch, C. Cuevas, M. Álvarez, and F. Albericio J. Am. Chem. Soc. 129 2007 5322
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 5322
- Tulla-Puche, J.¹ Bayó-Puxan, N.² Moreno, J.A.³ Francesch, A.M.⁴ Cuevas, C.⁵ Álvarez, M.⁶ Albericio, F.⁷

24
- 0344392796
- A.K. Galande, and A.F. Spatola Org. Lett. 5 2003 3431
- (2003) Org. Lett. , vol.5 , pp. 3431
- Galande, A.K.¹ Spatola, A.F.²

25
- 0037078808
- X. Tian, and E. Wickstrom Org. Lett. 4 2002 4013
- (2002) Org. Lett. , vol.4 , pp. 4013
- Tian, X.¹ Wickstrom, E.²

26
- 0033061086
- D. Sahal J. Pept. Res. 53 1999 91
- (1999) J. Pept. Res. , vol.53 , pp. 91
- Sahal, D.¹

27
- 0031878131
- D. Limal, J.-P. Briand, P.P. Dalbon, and M. Jolivet J. Pept. Res. 52 1998 121
- (1998) J. Pept. Res. , vol.52 , pp. 121
- Limal, D.¹ Briand, J.-P.² Dalbon, P.P.³ Jolivet, M.⁴

28
- 0034676702
- T. Zoller, J.-B. Ducep, C. Tahtaoui, and M. Hibert Tetrahedron Lett. 41 2000 9989
- (2000) Tetrahedron Lett. , vol.41 , pp. 9989
- Zoller, T.¹ Ducep, J.-B.² Tahtaoui, C.³ Hibert, M.⁴

29
- 0030575605
- S.E. Osborne, and A.D. Ellington Bioorg. Med. Chem. Lett. 6 1996 2339
- (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 2339
- Osborne, S.E.¹ Ellington, A.D.²

30
- 41649084341
- H. Ahn, W. Cho, J. Kim, B.P. Joshi, J. Park, C.R. Lohani, H. Cho, and K.-H. Lee Bioorg. Med. Chem. 16 2008 4127
- (2008) Bioorg. Med. Chem. , vol.16 , pp. 4127
- Ahn, H.¹ Cho, W.² Kim, J.³ Joshi, B.P.⁴ Park, J.⁵ Lohani, C.R.⁶ Cho, H.⁷ Lee, K.-H.⁸

31
- 17144390214
- A.K. Galande, R. Weissleder, and C.-H. Tung J. Comb. Chem. 7 2005 174
- (2005) J. Comb. Chem. , vol.7 , pp. 174
- Galande, A.K.¹ Weissleder, R.² Tung, C.-H.³

32
- 78651110462
- S. Thurow, V.A. Pereira, D.M. Martinez, D. Alves, G. Perin, R.G. Jacob, and E.J. Lenardão Tetrahedron Lett. 52 2011 640
- (2011) Tetrahedron Lett. , vol.52 , pp. 640
- Thurow, S.¹ Pereira, V.A.² Martinez, D.M.³ Alves, D.⁴ Perin, G.⁵ Jacob, R.G.⁶ Lenardão, E.J.⁷

33
- 33646518339
- E.L. Ruggles, and R.J. Hondal Tetrahedron Lett. 47 2006 4281
- (2006) Tetrahedron Lett. , vol.47 , pp. 4281
- Ruggles, E.L.¹ Hondal, R.J.²

34
- 0035829003
- T. Shi, and D.L. Rabenstein Tetrahedron Lett. 42 2001 7203
- (2001) Tetrahedron Lett. , vol.42 , pp. 7203
- Shi, T.¹ Rabenstein, D.L.²

35
- 58149339548
- E.L. Ruggles, P.B. Deker, and R.J. Hondal Tetrahedron 65 2009 1257
- (2009) Tetrahedron , vol.65 , pp. 1257
- Ruggles, E.L.¹ Deker, P.B.² Hondal, R.J.³

36
- 0027293130
- H. Tamamura, A. Otaka, J. Nakamura, K. Okubo, T. Koide, K. Ikeda, and N. Fujii Tetrahedron Lett. 34 1993 4931
- (1993) Tetrahedron Lett. , vol.34 , pp. 4931
- Tamamura, H.¹ Otaka, A.² Nakamura, J.³ Okubo, K.⁴ Koide, T.⁵ Ikeda, K.⁶ Fujii, N.⁷

37
- 0036811238
- T.J. Dickerson, N.N. Reed, and K.D. Janda Chem. Rev. 102 2002 3325
- (2002) Chem. Rev. , vol.102 , pp. 3325
- Dickerson, T.J.¹ Reed, N.N.² Janda, K.D.³

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

39
- 65249131079
- D.E. Bergbreiter, J. Tian, and C. Hongfa Chem. Rev. 109 2009 530
- (2009) Chem. Rev. , vol.109 , pp. 530
- Bergbreiter, D.E.¹ Tian, J.² Hongfa, C.³

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

41
- 0036061371
- K. Chiba, Y. Kono, S. Kim, K. Nishimoto, Y. Kitano, and M. Tada Chem. Commun. 2002 1766
- (2002) Chem. Commun. , pp. 1766
- Chiba, K.¹ Kono, Y.² Kim, S.³ Nishimoto, K.⁴ Kitano, Y.⁵ Tada, M.⁶

42
- 28644443614
- K. Hayashi, S. Kim, Y. Kono, M. Tamura, and K. Chiba Tetrahedron Lett. 47 2005 171
- (2005) Tetrahedron Lett. , vol.47 , pp. 171
- Hayashi, K.¹ Kim, S.² Kono, Y.³ Tamura, M.⁴ Chiba, K.⁵

43
- 39149085338
- S. Kim, K. Yamamoto, K. Hayashi, and K. Chiba Tetrahedron 64 2008 2855
- (2008) Tetrahedron , vol.64 , pp. 2855
- Kim, S.¹ Yamamoto, K.² Hayashi, K.³ Chiba, K.⁴

44
- 41549107085
- S. Kim, A. Tsuruyama, A. Ohmori, and K. Chiba Chem. Commun. 2008 1816
- (2008) Chem. Commun. , pp. 1816
- Kim, S.¹ Tsuruyama, A.² Ohmori, A.³ Chiba, K.⁴

45
- 68549115320
- K. Chiba, M. Sugihara, K. Yoshida, Y. Mikami, and S. Kim Tetrahedron 65 2009 8014
- (2009) Tetrahedron , vol.65 , pp. 8014
- Chiba, K.¹ Sugihara, M.² Yoshida, K.³ Mikami, Y.⁴ Kim, S.⁵

46
- 70349910271
- M. Iijima, Y. Mikami, T. Yoshioka, S. Kim, H. Kamiya, and K. Chiba Langmuir 25 2009 11043
- (2009) Langmuir , vol.25 , pp. 11043
- Iijima, M.¹ Mikami, Y.² Yoshioka, T.³ Kim, S.⁴ Kamiya, H.⁵ Chiba, K.⁶

47
- 77958513278
- G. Tana, S. Kitada, S. Fujita, Y. Okada, S. Kim, and K. Chiba Chem. Commun. 46 2010 8219
- (2010) Chem. Commun. , vol.46 , pp. 8219
- Tana, G.¹ Kitada, S.² Fujita, S.³ Okada, Y.⁴ Kim, S.⁵ Chiba, K.⁶

48
- 79960366834
- I. Friligou, E. Papadimitriou, D. Gatos, J. Matsoukas, and T. Tselios Amino Acids 40 2011 1431
- (2011) Amino Acids , vol.40 , pp. 1431
- Friligou, I.¹ Papadimitriou, E.² Gatos, D.³ Matsoukas, J.⁴ Tselios, T.⁵

49
- 77951127711
- D.G. Mullen, B. Weigel, G. Barany, and M.D. Distefano J. Pept. Sci. 16 2010 219
- (2010) J. Pept. Sci. , vol.16 , pp. 219
- Mullen, D.G.¹ Weigel, B.² Barany, G.³ Distefano, M.D.⁴

50
- 57349180472
- S. Zhang, F. Lin, M.A. Hossain, F. Shabanpoor, G.W. Tregear, and J.D. Wade Int. J. Pept. Res. Ther. 14 2008 301
- (2008) Int. J. Pept. Res. Ther. , vol.14 , pp. 301
- Zhang, S.¹ Lin, F.² Hossain, M.A.³ Shabanpoor, F.⁴ Tregear, G.W.⁵ Wade, J.D.⁶

51
- 60149105961
- A.S. Galanis, F. Albericio, and M. Grotli Biopolymers 92 2009 23
- (2009) Biopolymers , vol.92 , pp. 23
- Galanis, A.S.¹ Albericio, F.² Grotli, M.³

52
- 0141631635
- A. Cuthbertson, and B. Indrevoll Org. Lett. 5 2003 2955
- (2003) Org. Lett. , vol.5 , pp. 2955
- Cuthbertson, A.¹ Indrevoll, B.²

53
- 0026763134
- K. Akaji, T. Tatsumi, M. Yoshida, T. Kimura, Y. Fujiwara, and Y. Kiso J. Am. Chem. Soc. 114 1992 4137
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 4137
- Akaji, K.¹ Tatsumi, T.² Yoshida, M.³ Kimura, T.⁴ Fujiwara, Y.⁵ Kiso, Y.⁶

54
- 0016690441
- N. Fujii, and H. Yajima Chem. Pharm. Bull. 23 1975 1596
- (1975) Chem. Pharm. Bull. , vol.23 , pp. 1596
- Fujii, N.¹ Yajima, H.²

55
- 0016065485
- J.E.F. Rivier J. Am. Chem. Soc. 96 1974 2986
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 2986
- Rivier, J.E.F.¹

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