Solid-Phase Staudinger Ligation from a Novel Core-Shell-Type Resin:  A Tool for Facile Condensation of Small Peptide Fragments

Abstract

[reaction: see text] Solid-phase Staudinger ligation of small peptides was performed on a novel core-shell-type resin. Solid-phase Staudinger ligation was mediated by synthetic solid-supported phosphinothiol, which was readily prepared by a straightforward synthetic route. This protocol afforded final peptide products in excellent yields and purities and thus could provide the opportunity to facilitate a simple manipulation for condensation of peptide fragments. In particular, the resulting resin could be recycled in a successful manner.

Metabolic precision labeling enables selective probing of O-linkedN-acetylgalactosamine glycosylation

“…To a stirred solution of acid ( S )-2-azidopropionic acid(30) (1.7 g, 14.8 mmol) in MeOH (60 mL) were added D-glucosamine hydrochloride (1.32 g, 6.1 mmol) and triethylamine (2.28 mL, 16.28 mmol). The solution was cooled to 0 °C, and EDC (2.53 g, 16.28 mmol) and HOBt (1.13 g, 7.4 mmol) were added.…”

Staudinger Ligation as a Method for Bioconjugation

“…[88] To circumvent the troublesome purification often encountered after peptide synthesis using the Staudinger ligation, Kim et al developed a solid-phase Staudinger ligation strategy for the preparation of small peptides (Scheme 25). [89] The Staudinger ligation could successfully be performed with a modified HiCore resin. After regeneration, the solid support could be reused up to five times without a loss of performance.…”

One‐step radiosynthesis of 4‐[18F]flouro‐3‐nitro‐N‐2‐propyn‐1‐yl‐benzamide ([18F]FNPB): a new stable aromatic porosthetic group for efficient labeling of peptides with fluorine‐18

“…The product was obtained from another round of EA extractions (3 × 20 mL). These EA extracts were combined, dried (on MgSO 4 ), and evaporated to dryness giving 753‐mg pale yellow oils in 80% yield with no need for further purification …”