Journal
TETRAHEDRON LETTERS
Volume 58, Issue 24, Pages 2374-2377Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2017.05.007
Keywords
Stapled peptide; Unnatural amino acids; Asymmetric synthesis; Ni(II)-complex
Categories
Funding
- CAMS Innovation Funds for Medical Sciences (CIFMS) [2016-I2M-3-008, 2016-I2M-3-009]
- Fundamental Research Funds for the Central Institutes [2015CX08]
Ask authors/readers for more resources
The procedures for the synthesis of various alpha-alkenyl and alkyne amino acids were systematically optimized in light of enhancing atom economy, reducing hazardous reagent usage, and simplifying workup. By starting with Boc-Pro-OH and coupling with EDCl/DMAP followed by alkylation, chiral auxiliary was synthesized with high yield and enantioselectivity. For alkylation of the chiral complex, tBuONa was found and proved by quantitative calculation to be superior to tBuOK in generating more nucleophilic enolate salt, thereby can significantly enhance yield under room temperature. Final Fmoc protection was also dramatically facilitated in one-pot sequential manner by adding EDTA-2Na as the nickel chelator. Synthesis of alpha-bisalkenyl amino acid was also accomplished by achiral complex approach with high yield and efficacy. Accordingly, five most commonly used N-Fmoc protected alpha-alkenyl and alkynyl amino acids were synthesized and characterized. (C) 2017 Published by Elsevier Ltd.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available