45101-25-5Relevant academic research and scientific papers
Efficient asymmetric synthesis of N-protected-β-aryloxyamino acids via regioselective ring opening of serine sulfamidate carboxylic acid
Malhotra, Rajesh,Dey, Tushar K.,Dutta, Swarup,Basu, Sourav,Hajra, Saumen
, p. 6507 - 6515 (2014/08/18)
First regioselective ring opening of serine derived cyclic sulfamidate by hard nucleophiles like ArONa is developed, where β-elimination of serine sulfamidate ester by stronger nucleophiles is overcome by reversal of the electronic effect of the carboxyla
Novel amino acids: Synthesis of furoxan and sydnonimine containing amino acids and peptides as potential nitric oxide releasing motifs
Nortcliffe, Andrew,Botting, Nigel P.,O'Hagan, David
, p. 4657 - 4671 (2013/07/26)
The incorporation of furoxan and sydnonimine ring systems into amino acid side chains is demonstrated with the preparation of four novel amino acids which carry these nitric oxide-releasing motifs. N-((4-Nitrophenoxy)carbonyl)-3- phenylsydnonimine 9 and bis(phenylsulfonyl)furoxan 10 are the key intermediates for introducing the heterocycle side chains onto appropriate amine and alcohol functionalities respectively. Furoxan 5 and 7 both displayed NO release based on determination of nitrite production. Orthogonal amino acid protecting group strategies were deployed to demonstrate that the amino acids could be incorporated into peptide frameworks. By way of demonstration the amino acids were placed centrally into several tripeptide motifs. Griess test assays showed that these amino acids released NO in the presence of γ-glutathione (GST). is
PHOSPHORORGANISCHE VERBINDUNGEN 109 DIE SYNTHESE FLUORESZIERENDER REAGENTIEN MIT CHEMOSELEKTIVEN ANKERGRUPPEN
Horner, Leopold,Hallenbach, Werner
, p. 173 - 188 (2007/10/02)
A route for the synthesis of type B-compounds is reported.Compound 5 is a strong fluorescent and is O-selective.Type C-compounds, for example 10a to 10d show a high fluorescence and are O-selective.They are obtained via 6 and 7 (n = 2-4, 6; R = Me, X = F).Boc-serine is O-phosphonylated by the methyl-phophonicacid-esterfluorides, for example 10c. ω-(9-Acridinyl)alkyl-phosphonicacid-alkylesterfluorides, like 22, are available in only moderate yields via 15a-e as intermediates.More but unsuccesful experiments for the synthesis of fluorescent and O-selective acridine compounds are reported shortly.
A Useful and Biomimetic Synthesis of N-Acyl α,β-Dehydroalanine form Aspartic Acid
Seki, Masahiko,Moriya, Tamon,Matsumoto, Kazuo
, p. 1251 - 1256 (2007/10/02)
N-Acyl α,β-dehydroalanines (1) were synthesized from the corresponding N-acyl aspartic acids by a one-pot procedure through a biomimetic oxidative β-decarboxylation.In particular, the transformation using methanol-sodium hypochlorite aqueous solution, which served for N-chlorination and dehydrochlorination, afforded good yields of (1).
