Application of the 2-(phenylsulfonyl)ethoxycarbonyl Group for the ε-Amino Function of Lysine in Liquid Phase Peptide Synthesis

Bulletin of the Korean Chemical Society

Volumn 19, Issue 6, 1998, Pages 696-698

  Lee, Yeon Sun ^a   Lee, Hyun Jin ^a   Pozdnyakov, Pavel I ^a   Samukov, Vladimir V ^a   Kim, Hack Joo ^a  

^a NONE

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EID: 0009776567     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (18)

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2. (b) Yamashiro, D.; Li, C. ibid. 1973, 95, 1310
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6. Verhart, C. G. J.; Tesser, G. I. Reci. Trav. Chim. Pays-Bas 1988, 107, 621
7. Samukov, V. V.; Savirov, A. N.; Pozdnyakov, P. I. Tetrahedron Lett. 1994, 35, 7821.
8. 2(c) and 2(d). These authors demonstrated that substituent excelling negative inductive effect could facilitate the removal of the protecting group by β-elimination.
9. (a)Ishida, S. Agric. and Biol. Chem.(Japan) 1966, 30, 800
10. (b) Tesser, G. F.; Balvert-Geers, I. C. Int. J. Peptiide Protein Res. 1975, 7, 295
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12. (a) Kurtz, A. C. J. Biol. Chem. 1941, 140, 705
13. (b) Roeske, R., Stewart, F. H. C.; Stedman, R. J., du Vigneaud, V. J. Am. Chem. Soc. 1956, 78, 5883.
14. Toennies, G.; Kolb, J. J. J. Biol. Chem. 1941, 140, 131.
15. 2 (1,7-disulfide bond)
16. After completion of the peptide chain (1-32) by fragment assembly, and deprotection of the Boc group, the resulting side chain-protected peptide chain was treated with piperidine in DMSO for 5 min to afford crude salmon calcitonin, which was purified by preparative HPLC (C-18, LiChrospher 300, 15 μm, 50×250 mm. column for packing stand NW 50; gradient 20% to 50% of acetonitrile (0.2% TFA) in 30 min; 30 mL/min; 214 nm) in a purity of >98% according to analytical HPLC. The purified one showed high hypocalcemic potency of about 4000 IU/mg measured in rats by MRC method.
17. 4. The procedure will be discussed in detail elsewhere.
18. Sarin, V. K.; Kent, S. B. H.; Tam, J. P.; Merrifield, R. B. Anal. Biochem. 1981, 117, 147.