117835-13-9Relevant academic research and scientific papers
Soluble and reusable poly(norbornene) supports with high loading capacities for peptide synthesis
Naganna, Nimmashetti,Madhavan, Nandita
, p. 5870 - 5873 (2013/12/04)
Poly(norbornene) supports comprising solubilizing ethylene glycol units and multiple amino acid attachment sites have been developed for peptide synthesis. A variety of amino acids have been efficiently loaded (0.6-1.1 mmol/g) onto the support in high yields (83-98%). Several tripeptides have been synthesized in moderate-to-good overall yields (41-66%) using only 1.2 equiv of coupling reagents/amino acids, and the support could be efficiently recycled up to 3 times.
Natural amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions
Bueno, Maria P.,Cativiela, Carlos,Mayoral, Jose A.,Avenoza, Alberto,Charro, Paula,et al.
, p. 2826 - 2829 (2007/10/02)
To test whether α-amino acids can be efficient chiral auxiliaries in asymmetric Diels-Alder reactions, the chiral dienophile N-acryloyl-L-phenylalanine methyl ester was made to react with cyclopentadiene.Diastereofacial selectivity is to a great extent dependent on the Lewis acid used to promote the reaction; whereas moderate excesses of the (1R,2R)-cycloadduct were achieved with AlCl3, the reaction did not show diastereofacial selectivity when titanium catalysts were used.Moreover, with Ti(iPrO)4 a transesterification reaction, which leads to the isopropyl ester and competes with the Diels-Alder reaction, was observed.In spite of the stuctural similarity of this dienophile to the acrylate of (S)-ethyl lactate, it behaved very differently in the titanium-catalyzed reactions.
