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. Author manuscript; available in PMC: 2016 Oct 14.
Published in final edited form as: J Am Chem Soc. 2015 Oct 1;137(40):13167–13175. doi: 10.1021/jacs.5b08754

Scheme 1. Preliminary Approach to G-CSF 1–174 (2a) by Conventional Meansa.

Scheme 1

aReagents and conditions: (a) 1.5 equiv of 4 and 1.0 equiv of 5, 6 M Gnd·HCl, 300 mM Na2HPO4, 20 mM TCEP, pH 7.2, isolated 6 (38%); (b) 1 equiv of 7 and 1.1 equiv of 8, 6 M Gnd·HCl, 300 mM Na2HPO4, 20 mM TCEP, 200 mM MPAA, pH 7.6, isolated 9a (14%); (c) 9a, VA-044, t-BuSH, TCEP, solvent (see the Supporting Information); TCEP = tris(2-carboxyethyl)phosphine, MPAA = 4-mercaptophenylacetic acid, VA-044 = 2,2′-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride.