Backbone cyclic insulin

Journal of Peptide Science

Volumn 16, Issue 9, 2010, Pages 473-479

  Andersen, Asser S ^a   Palmqvist, Eva ^a   Bang, Susanne ^a   Shaw, Allan C ^a   Hubalek, Frantisek ^a   Ribel, Ulla ^a   Hoeg Jensen, Thomas ^a  

^a NOVO NORDISK A S   (Denmark)

Author keywords

Achromobacter lyticus protease; Carboxypeptidase Y; Cyclic; Insulin; Semi synthesis; Wistar rats

Indexed keywords

C PEPTIDE; CHYMOTRYPSIN; DISULFIDE; INSULIN; LYSINE;

ACHROMOBACTER; AMINO TERMINAL SEQUENCE; ANIMAL EXPERIMENT; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL BOND; CONTROLLED STUDY; CYCLIZATION; DEGRADATION; LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN ENGINEERING; PROTEIN EXPRESSION; RAT; RECEPTOR AFFINITY; RING CLOSING METATHESIS; WISTAR RAT; YEAST;

AMINO ACID SEQUENCE; ANIMALS; CHROMATOGRAPHY, LIQUID; CYCLIZATION; INSULIN; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; PEPTIDES, CYCLIC; RATS; RATS, WISTAR; RECEPTOR, INSULIN;

ACHROMOBACTER LYTICUS; RATTUS NORVEGICUS;

EID: 77957295369     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1264     Document Type: Article

References (27)

1. Jackson DY, Burnier JP, Wells JA. Enzymatic cyclization of linear peptide esters using subtiligase. J. Am. Chem. Soc. 1995; 117: 819-820.
2. Antos JM, Popp MWL, Ernst R, Chew GL, Spooner E, Ploegh HL. A straight path to circular proteins. J. Biol. Chem. 2009; 284: 16028-16036.
3. Botos I, Wu Z, Lu W, Wlodawer A. Crystal structure of a cyclic form of bovine pancreatic trypsin inhibitor. FEBS Lett. 2001; 509: 90-94.
4. Jiang S, Li Z, Ding K, Roller PP. Recent progress of synthetic studies to peptide and peptidomimetic cyclization. Curr. Org. Chem. 2008; 12: 1502-1542.
5. Grunewald J, Marahiel MA. Chemoenzymatic and template-directed synthesis of bioactive macrocyclic peptides. Microbiol. Mol. Biol. Rev. 2006; 70: 121-146.
6. Trabi M, Craik DJ. Circular proteins - no end in sight. Trends Biochem. Sci. 2002; 27: 132-138.
7. Iwai H, Lingel A, Pluckthun A. Cyclic green fluorescent protein produced in vivo using an artificially split PI-PfuI intein from Pyrococcus furiosus. J. Biol. Chem. 2001; 276: 16548-16554.
8. Evans TC Jr, Benner J, Xu MQ. The cyclization and polymerization of bacterially expressed proteins using modified self-splicing inteins. J. Biol. Chem. 1999; 274: 18359-18363.
9. Camarero JA, Fushman D, Sato S, Giriat I, Cowburn D, Raleigh DP, Muir TW. Rescuing a destabilized protein fold through backbone cyclization. J.Mol. Biol. 2001; 308: 1045-1062.
10. Yan LZ, Dawson PE. Design and synthesis of a protein catenane. Angew. Chem. Int. Ed. 2001; 40: 3625-3627.
11. Morihara K. Enzymatic semisynthesis of human insulin: an update. J. Mol. Recogn. 1990; 3: 181-186.
12. Markussen J, Damgaard U, Pingel M, Snel L, Sørensen AR, Sørensen E. Human insulin Novo: chemistry and characteristics. Diabetes Care 1983; 6 S1: 4-8. (Pubitemid 13159772)
13. Markussen J, Jørgensen KH, Sørensen AR, Tochino Y. Single chain des-(B30) insulin. Intramolecular crosslinking of insulin by trypsin-catalyzed transpeptidation. Int. J. Pept. Protein Res. 1985; 26: 70-77.
14. Steiner DF. The biosynthesis of insulin. In Pancreatic Beta Cell in Health and Disease, Seino S, Bell GI (eds.). Springer: Japan, 2008; 31-49.
15. Steiner DF. Proinsulin and the biosynthesis of insulin. N. Engl. J. Med. 1969; 280: 1106-1113.
16. Kjeldsen T. Yeast secretory expression of insulin precursors. Appl. Microbiol. Biotechnol. 2000; 54: 277-286.
17. Chang SG, Kim DY, Choi KD, Shin JM, Shin HC. Human insulin production from a novel mini-proinsulin which has high receptor-binding activity. Biochem J. 1998; 329: 631-635.
18. Kjeldsen TB, Andersen AS, Sørensen AR, Schlein M, Madsen P. Single-chain insulins, patent application WO2005054291.
19. Hua QX, Nakagawa SH, Jia W, Huang K, Phillips NB, Hu SQ, Weiss MA. Design of an active ultrastable single-chain insulin analog - synthesis, structure, and therapeutic implications. J. Biol. Chem. 2008; 283: 14703-14716.
20. Heath WF, Belagaje RM, Brooke GS, Chance RE, Hoffmann JA, Long HB, Reams SG, Roundtree C, Shaw WN, Slieker LJ, Sundell KL, DiMarchi RD. (A-C-B) human proinsulin, a novel insulin agonist and intermediate in the synthesis of biosynthetic human insulin. J. Biol. Chem. 1992; 267: 419-425.
21. Ribel U, Hougaard P, Drejer K, Sørensen AR. Equivalent in vivo biological activity of insulin analogues and human insulin despite different in vitro potencies. Diabetes 1990; 39: 1033-1039.
22. Verduyn C, Postma E, Scheffers WA, van Dijken JP. Physiology of Saccharomyces cerevisiae in anaerobic glucose-limited chemostat cultures. J. Gen.Microbiol. 1990; 136: 395-403. (Pubitemid 20109730)
23. Chu YC, Zong L, Burke GT, Katsoyannis PG. The A14 position of insulin tolerates considerable structural alterations with modest effects on the biological behavior of the hormone. J. Protein Chem. 1992; 11: 571-577.
24. Kjeldsen T, Brandt J, Andersen AS, Egel-Mitani M, Hach M, Pettersson AF, Vad K. A removable spacer peptide in an alpha-factor- leader/insulin precursor fusion protein improves processing and concomitant yield of the insulin precursor in Saccharomyces cerevisiae. Gene 1996; 170: 107-112. (Pubitemid 26130804)
25. Olesen K, Mortensen UH, Aasmul-Olsen S, Kielland-Brandt MC, Remington SJ, Breddam K. The activity of carboxypeptidase Y toward substrates with basic P1 amino acid residues is drastically increased by mutational replacement of leucine 178. Biochemistry 1994; 33: 11121-11126. (Pubitemid 24304276)
26. Glendorf T, Sørensen AR, Nishimura E, Pettersson I, Kjeldsen T. Importance of the solvent-exposed residues of the insulin B chain alpha-helix for receptor binding. Biochemistry 2008; 47: 4743-4751.
27. Wollmer A, Gilge G, Brandenburg D, Gattner HG. An insulin with the native sequence but virtually no activity. Biol. Chem. Hoppe Seyler 1994; 375: 219-222.