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. Author manuscript; available in PMC: 2011 Mar 27.
Published in final edited form as: Tetrahedron. 2010 Mar 27;66(13):2277–2283. doi: 10.1016/j.tet.2010.01.067

Table 1.

Threonine extension by coupling and subsequent free-radical desulfurization

graphic file with name nihms-180739-t0003.jpg

Entry Peptide Coupling Product/Yield/Time Desulfurization Product/Yield/Time
1 graphic file with name nihms-180739-t0004.jpg graphic file with name nihms-180739-t0005.jpg FmocRNEDLSGAT—OMe
9 / 92 % / 2 h
2 graphic file with name nihms-180739-t0006.jpg graphic file with name nihms-180739-t0007.jpg FmocRLGDSTAGQT—OMe
12 / 81% / 2 h
3 graphic file with name nihms-180739-t0008.jpg graphic file with name nihms-180739-t0009.jpg FmocRLGDSTAGYT—OMe
15 / 89% / 2 h
4 graphic file with name nihms-180739-t0010.jpg graphic file with name nihms-180739-t0011.jpg FmocRLGDSTAGWT—OMe
18 / 90% / 2 h
5 graphic file with name nihms-180739-t0012.jpg graphic file with name nihms-180739-t0013.jpg FmocRTGDSAGTT—OMe
21 / 84% / 2 h
6 graphic file with name nihms-180739-t0014.jpg graphic file with name nihms-180739-t0015.jpg FmocRLGDSTAGLT—OMe
24 / 80% / 2 h
7 graphic file with name nihms-180739-t0016.jpg graphic file with name nihms-180739-t0017.jpg FmocKYDSRGFT—OMe
27 / 80% / 2 h
8 graphic file with name nihms-180739-t0018.jpg graphic file with name nihms-180739-t0019.jpg FmocRTGDSAGVT—OMe
30 / 95% / 2 h
9 graphic file with name nihms-180739-t0020.jpg graphic file with name nihms-180739-t0021.jpg FmocRTGDSAGIT—OMe
33 / 82% / 2 h
10 graphic file with name nihms-180739-t0022.jpg graphic file with name nihms-180739-t0023.jpg FmocVRSYTAGPT—OMe
36 / 83% / 2 h

Key: (a) buffer at pH 6.5 (6.0 M Gn·HCl, 188.8 mM Na2HPO4), TCEP, rt (b) TCEP, VA-044, tBuSH, 37 °C. VA-044=2,2′-azobis-[2-(2-imidazolini-2-yl)propane] dihydrochloride.

TCEP=tris(2-carboxyethyl)phosphine.