A novel post-ligation thioesterification device enables peptide ligation in the N to C direction: Synthetic study of human glycodelin

Journal of Peptide Science

Volumn 20, Issue 1, 2014, Pages 55-61

  Takenouchi, Takaomi ^a   Katayama, Hidekazu ^a   Nakahara, Yuko ^a   Nakahara, Yoshiaki ^a   Hojo, Hironobu ^a,b  

^a TOKAI UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

glycodelin; N alkylcysteine; native chemical ligation; peptide thioester; thioesterification

Indexed keywords

9 FLUORENYLMETHOXYCARBONYL; CARBONYL DERIVATIVE; CYSTEINE DERIVATIVE; HOMOCYSTEINE; LEUCINE; METHIONINE; N ETHYL ACETAMIDOMETHYL CYSTEINE; PLACENTA PROTEIN 14; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; DEPROTECTION REACTION; ESTERIFICATION; METHYLATION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; SOLID PHASE SYNTHESIS;

GLYCODELIN; N-ALKYLCYSTEINE; NATIVE CHEMICAL LIGATION; PEPTIDE THIOESTER; THIOESTERIFICATION;

AMINO ACID SEQUENCE; AMINO ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, REVERSE-PHASE; CYSTEINE; ESTERIFICATION; FLUORENES; GLYCOPROTEINS; HUMANS; SOLID-PHASE SYNTHESIS TECHNIQUES;

EID: 84890893373     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.2592     Document Type: Article

References (30)

1. Lapid K, Sharon N,. Glycobiology 2006; 16: 39R-45R.
2. Gaudiano MC, Pala A, Barteri M,. Biochem. Biophys. Acta 1999; 1431: 451-461.
3. Dell A, Morris HR, Easton RL, Panico M, Patankar M, Oehninger S, Koistinen R, Koistinene H, Seppala M, Clark GF,. J. Biol. Chem. 1995; 270: 24116-24126.
4. Morris HR, Dell A, Easton RL, Panico M, Koistinen H, Koistinene R, Oehninger S, Patankar MS, Seppala M, Clark GF,. J. Biol. Chem. 1996; 271: 32159-32167.
5. Lee C-L, Pang P-C, Yeung WSB, Tissot B, Panico M, Lao TTH, Chu IK, Lee K-F, Chung M-K, Lam KKW, Koistinen R, Koistinen H, Seppälä M, Morris HR, Dell A, Chiu PCN,. J. Biol. Chem. 2009; 284: 15084-15096.
6. Seppälä M, Koistinen H, Koistinen R, Hautala L, Chiu PC, Yeung WS,. Eur. J. Endocrinol. 2009; 160: 121-133.
7. Van den Nieuwenhof IM, Koistinen H, Easton RL, Koistinen R, Kämäräinen M, Morris HR, van Die I, Seppälä M, Dell A, Van den Eijnden DH,. Eur. J. Biochem. 2000; 267: 4753-4762.
8. Mukhopadhyay D, SundarRaj S, Alok A, Karande AA,. J. Biol. Chem. 2004; 279: 8577-8584.
9. Poornima BL, Karande AA,. FEBS Lett. 2007; 581: 4366-4370.
10. Dawson PE, Muir TW, Clark-Lewis I, Kent SBH,. Science 1994; 266: 776-779.
11. Saporito A, Marasco D, Chambery A, Botti P, Monti SM, Pedone C, Ruvo M,. Biopolymers 2006; 83: 508-518.
12. Bang D, Pentelute BL, Kent SBH,. Angew. Chem. Int. Ed. 2006; 45: 3985-3988.
13. Kawakami T, Aimoto S,. Tetrahedron Lett. 2007; 48: 1903-1905.
14. Shigenaga A, Sumikawa Y, Tsuda S, Sato K, Otaka A,. Tetrahedron 2010; 66: 3290-3296.
15. Sato K, Shigenaga A, Kitakaze K, Sakamoto K, Tsuji D, Itoh K, Otaka A,. Angew. Chem. Int. Ed. 2013; 52: 7855-7859.
16. Hojo H, Onuma Y, Akimoto Y, Nakahara Y, Nakahara Y,. Tetrahedron Lett. 2007; 48: 25-28.
17. Ozawa C, Katayama H, Hojo H, Nakahara Y, Nakahara Y,. Org. Lett. 2008; 10: 3531-3533.
18. Erlich LA, Kumar KSA, Haj-Yahya M, Dawson PE, Brik A. Org. Biomol. Chem. 2010; 8: 2392-2396.
19. Huang W, Li C, Li B, Umekawa M, Yamamoto K, Zhang X, Wang L-X,. J. Am. Chem. Soc. 2009; 131: 2214-2223.
20. (a), Hojo H, Tanaka H, Hagiwara M, Asahina Y, Ueki A, Katayama H, Nakahara Y, Yoneshige A, Matsuda J, Ito Y, Nakahara Y,. J. Org. Chem. 2012; 77: 9437-9446
21. (b), Asahina Y, Kamitori S, Takao T, Nishi N, Hojo H,. Angew. Chem. Int. Ed. 2013; 52: 9733-9737.
22. Katayama H, Hojo H, Ohira T, Ishii A, Nozaki T, Goto K, Nakahara Y, Takahashi T, Hasegawa Y, Nagasawa H, Nakahara Y,. Biochemistry 2010; 49: 1798-1807.
23. Nakahara Y, Matsuo I, Ito S, Ubagai R, Hojo H, Nakahara Y,. Tetrahedron Lett. 2010; 51: 407-410.
24. (a), Villain M, Vizzavona J, Rose K,. Chem. Biol. 2001; 8: 673-679
25. (b), Villain M, Vizzavona J, Gaertner H,. Proc. second int. seventeenth Am. peptide symp. 2001; 107-108.
26. (a), Tam JP, Heath WF, Merrifield RB,. J. Am. Chem. Soc. 1986; 108: 5242-5251
27. (b), Hojo H, Haginoya E, Matsumoto Y, Nakahara Y, Nabeshima K, Toole BP, Watanabe Y,. Tetrahedron Lett. 2003; 44: 2961-2964
28. (c), Takano Y, Hojo H, Kojima N, Nakahara Y,. Org. Lett. 2004; 6: 3135-3138
29. (d), Hojo H, Matsumoto Y, Nakahara Y, Ito Y, Suzuki Y, Suzuki M, Suzuki A, Nakahara Y,. J. Am. Chem. Soc. 2005; 127: 13720-13725.
30. Hagiwara M, Dohi M, Nakahara Y, Komatsu K, Asahina Y, Ueki A, Hojo H, Nakahara Y, Ito Y,. J. Org. Chem. 2011; 76: 5229-39.