28069-46-7Relevant articles and documents
Regioselective Azide Opening of 2,3-Epoxy Alcohols by : Synthesis of α-Amino Acids
Caron, Maurice,Carlier, Paul R.,Sharpless, K. Barry
, p. 5185 - 5187 (1988)
Treatment of 2,3-epoxy alcohols with affords the corresponding 3-azido 1,2-diols, which are readily transformed in two steps to the α-amino acids.
LAT-1 activity of meta-substituted phenylalanine and tyrosine analogs
Augustyn, Evan,Finke, Karissa,Zur, Arik A.,Hansen, Logan,Heeren, Nathan,Chien, Huan-Chieh,Lin, Lawrence,Giacomini, Kathleen M.,Colas, Claire,Schlessinger, Avner,Thomas, Allen A.
supporting information, p. 2616 - 2621 (2016/05/09)
The transporter protein Large-neutral Amino Acid Transporter 1 (LAT-1, SLC7A5) is responsible for transporting amino acids such as tyrosine and phenylalanine as well as thyroid hormones, and it has been exploited as a drug delivery mechanism. Recently its role in cancer has become increasingly appreciated, as it has been found to be up-regulated in many different tumor types, and its expression levels have been correlated with prognosis. Substitution at the meta position of aromatic amino acids has been reported to increase affinity for LAT-1; however, the SAR for this position has not previously been explored. Guided by newly refined computational models of the binding site, we hypothesized that groups capable of filling a hydrophobic pocket would increase binding to LAT-1, resulting in improved substrates relative to parent amino acid. Tyrosine and phenylalanine analogs substituted at the meta position with halogens, alkyl and aryl groups were synthesized and tested in cis-inhibition and trans-stimulation cell assays to determine activity. Contrary to our initial hypothesis we found that lipophilicity was correlated with diminished substrate activity and increased inhibition of the transporter. The synthesis and SAR of meta-substituted phenylalanine and tyrosine analogs is described.
Recyclable Ligands for the Non-Enzymatic Dynamic Kinetic Resolution of Challenging α-Amino Acids
Nian, Yong,Wang, Jiang,Zhou, Shengbin,Wang, Shuni,Moriwaki, Hiroki,Kawashima, Aki,Soloshonok, Vadim A.,Liu, Hong
supporting information, p. 12918 - 12922 (2015/11/02)
Structurally simple and inexpensive chiral tridentate ligands were employed for substantially advancing the purely chemical dynamic kinetic resolution (DKR) of unprotected racemic tailor-made α-amino acids (TM-α-AAs), enabling the first DKR of TM-α-AAs bearing tertiary alkyl chains as well as multiple unprotected functional groups. Owing to the operationally convenient conditions, virtually complete stereoselectivity, and full recyclability of the source of chirality, this method should find wide applications for the preparation of TM-α-AAs, especially on large scale. The non-enzymatic dynamic kinetic resolution of racemic α-amino acids bearing tertiary alkyl chains and multiple unprotected functional groups is based on the enantioselective formation of nickel(II) complexes and their hydrolysis under convenient conditions. The specially designed chiral ligands are inexpensive and can be quantitatively recycled.
