82706-26-1Relevant articles and documents
Novel anti-β-functionalized γ,δ-unsaturated amino acids via a thio-Claisen rearrangement
Liu, Zhihua,Qu, Hongchang,Gu, Xuyuan,Lee, Kwang-Soo,Grossman, Bryan,Kumirov, Vlad K.,Hruby, Victor J.
supporting information; experimental part, p. 3518 - 3520 (2010/08/20)
A significantly improved thio-Claisen rearrangement method was developed for preparing anti-β-functionalized γ,δ-unsaturated amino acids, which are extremely useful nonproteinogenic amino acids used in chemistry and biology research. The mild reaction condition successfully introduced base labile functional groups into the amino acids with excellent anti/syn selectivities.
Evaluation of 3-substituted arginine analogs as selective inhibitors of human nitric oxide synthase isozymes
Ijuin, Ryosuke,Umezawa, Naoki,Nagai, Shin-Ichi,Higuchi, Tsunehiko
, p. 2881 - 2885 (2007/10/03)
Nitric oxide (NO), a mediator of various physiological and pathophysiological processes, is synthesized by three isozymes of nitric oxide synthase (NOS). In developing candidate clinical drugs, it is very important not to inhibit endothelial NOS, because
Ester-Enolate Claisen Rearrangement of α-Amino Acid Derivatives
Bartlett, Paul A.,Barstow, James F.
, p. 3933 - 3941 (2007/10/02)
With the standard procedure for the Ireland-Claisen rearrangement, using 2 equiv of base, allylic esters of N-acyl α-amino acids are converted to the rearranged γ,δ-unsaturated α-amino acids in moderate to good yield and diastereoselectivity.Moderate variation, but not reversal, of stereoselectivity is seen on using different solvents or conditions.Variation in the substituents on the amino group, α-position, and allylic alcohol moiety was also studied.For each case in which the stereochemistry of the rearranged product was proven, it was consistent with predominant formation of the E enolate (enolate oxygen and anionic acylamido substituent cis).The rearrangement was also apllied successfully to the synthesis of highly hindered amino acids and to cyclo-alkenyl-substituted analogues.In a number of instances, comparison was made with an alternative rearrangement procedure involving an oxazole intermediate.
