1197335-40-2Relevant academic research and scientific papers
Synthesis and Fluorescent Properties of β-Pyridyl α-Amino Acids
Harkiss, Alexander H.,Bell, Jonathan D.,Knuhtsen, Astrid,Jamieson, Andrew G.,Sutherland, Andrew
, p. 2879 - 2890 (2019/03/07)
The preparation of a new class of β-pyridyl α-amino acid is described using a highly regioselective, ytterbium-catalyzed hetero-Diels-Alder reaction of enones with vinyl ethers followed by a modified Knoevenagel-Stobbe reaction as the key heterocycle form
Synthesis of pyrazole containing α-amino acids via a highly regioselective condensation/aza-Michael reaction of β-aryl α,β-unsaturated ketones
Gilfillan, Lynne,Artschwager, Raik,Harkiss, Alexander H.,Liskamp, Rob M. J.,Sutherland, Andrew
, p. 4514 - 4523 (2015/04/14)
A synthetic approach for the preparation of a new class of highly conjugated unnatural α-amino acids bearing a 5-arylpyrazole side-chain has been developed. Horner-Wadsworth-Emmons reaction of an aspartic acid derived β-keto phosphonate ester with a range of aromatic aldehydes gave β-aryl α,β-unsaturated ketones. Treatment of these with phenyl hydrazine followed by oxidation allowed the regioselective synthesis of pyrazole derived α-amino acids. As well as evaluating the fluorescent properties of the α-amino acids, their synthetic utility was also explored with the preparation of a sulfonyl fluoride derivative, a potential probe for serine proteases.
Switching the stereochemical outcome of 6- endo - Trig cyclizations; Synthesis of 2,6- cis -6-substituted 4-oxopipecolic acids
Daly, Mark,Cant, Alastair A.,Fowler, Lindsay S.,Simpson, Graham L.,Senn, Hans Martin,Sutherland, Andrew
, p. 10001 - 10009 (2013/01/15)
A base-mediated 6-endo-trig cyclization of readily accessible enone-derived α-amino acids has been developed for the direct synthesis of novel 2,6-cis-6-substituted-4-oxo-l-pipecolic acids. A range of aliphatic and aryl side chains were tolerated by this mild procedure to give the target compounds in good overall yields. Molecular modeling of the 6-endo-trig cyclization allowed some insight as to how these compounds were formed, with the enolate intermediate generated via an equilibrium process, followed by irreversible tautomerization/neutralization providing the driving force for product formation. Stereoselective reduction and deprotection of the resulting 2,6-cis-6-substituted 4-oxo-l-pipecolic acids to the corresponding 4-hydroxy-l-pipecolic acids was also performed.
Synthesis of fluorescent enone derived α-amino acids
Fowler, Lindsay S.,Ellis, David,Sutherland, Andrew
experimental part, p. 4309 - 4316 (2009/12/06)
The development of a facile and general method for the preparation of enone derived α-amino acids is described. The key step involves a Horner-Wadsworth-Emmons reaction between an aspartic acid derived β-keto phosphonate ester and a range of aldehydes resulting in the formation of highly functionalised α-amino acids in good yields. An efficient two-stage deprotection process using mild conditions was developed to give the parent α-amino acids. Application of this methodology has produced a novel fluorescent α-amino acid that has potential as a biological marker.
