1. Sulfur protection with the 3-nitro-2-pyridinesulfenyl group in solid-phase peptide synthesis
- Author
-
Rei Matsueda, Richard J. Ridge, Edgar Haber, and Gary R. Matsueda
- Subjects
chemistry.chemical_classification ,chemistry.chemical_compound ,chemistry ,Reagent ,Size-exclusion chromatography ,Side chain ,Peptide synthesis ,Thiol ,Organic chemistry ,Anisole ,Biochemistry ,High-performance liquid chromatography ,Cysteine - Abstract
The 3-nitro-2-pyridinesulfenyl (Npys) group has been used successfully for side chain protection of cysteine during the stepwise solid-phase synthesis of Lys8-vasopressin (LVP) on benzhydrylamine resin. The versatility and limitations of this group have been evaluated by comparison of this synthesis with a parallel control synthesis using the 3,4-dimethylbenzyl (DMB) group and with a synthesis utilizing a combination of both groups. The Npys group was found to be stable to TFA as reported and, in addition, was found to be stable to HF: anisole (9:1) for 45 min at 0 degree, but not when thiol was present in either reagent. Furthermore, compatibility of the Npys group with the Boc-benzyl synthetic tactic in solid-phase peptide synthesis was demonstrated. LVP with full biological activity was obtained after purification by gel filtration and reverse-phase HPLC.
- Published
- 2009