92086-93-6Relevant articles and documents
A reappraisal of the Ni-[(Benzylprolyl)amino]benzophenone complex in the synthesis of α,α-disubstituted amino acid derivatives
Watson, Morag E.,Jamieson, Craig,Kennedy, Alan R.,Mason, Andrew M.
, (2019/08/08)
α,α-Disubstituted alkenyl amino acid derivatives (e.g. Fmoc-S5-OH) are valuable monomers in the construction of stapled peptide derivatives. Synthetic access to these is possible using the Ni-[(Benzylprolyl)amino]benzophenone (BPB) complex as a chiral auxiliary. We discuss a reappraisal of the use of this, and demonstrate that epimerisation of the proline α-centre occurs during formation of the complex, leading to erosion in the enantiomeric excess of the final product. Modified conditions have been developed, providing the target compounds in high enantiomeric excess.
A Convenient Method for the Asymmetric Synthesis of Fluorinated α-Amino Acids from Alcohols
Drouet, Fleur,Noisier, Anas F. M.,Harris, Craig S.,Furkert, Daniel P.,Brimble, Margaret A.
supporting information, p. 1195 - 1201 (2015/10/05)
Due to their numerous applications, fluorinated amino acids have recently attracted significant attention. The preparation of fluorine-containing phenylalanines, heteroaryl alanines and aliphatic fluorinated amino acids using Mitsunobu-Tsunoda alkylation of a chiral nucleophilic glycine equivalent with readily available alcohol substrates is described. The reaction proceeds in high yields and with excellent diastereoselectivity. This method provides an efficient synthetic route to fluorinated amino acids for which asymmetric approaches are scarce.
A One-Pot approach to neoglycopeptides using orthogonal native chemical ligation and click chemistry
Lee, Dong Jun,Mandai, Kalyaneswar,Harris, Paul W. R.,Brimble, Margaret A.,Kent, Stephen B. H.
supporting information; experimental part, p. 5270 - 5273 (2009/12/28)
The powerful combination of native chemical ligation and click chemistry has been used to affect a one-pot synthesis of neogiycopeptiaes from propargyl-containing peptides using GaINAc-N3 as the glycan component. A versatile chemical toolkit fo
