85452-41-1Relevant academic research and scientific papers
Gold-Catalyzed Amide/Carbamate-Linked N, O-Acetal Formation with Bulky Amides and Alcohols
Ohsawa, Kosuke,Ochiai, Shota,Kubota, Junya,Doi, Takayuki
, p. 1281 - 1291 (2021/01/14)
A gold-catalyzed N,O-acetal formation was established to construct an amide/carbamate-linked N,O-acetal substructure with bulky alcohols. The acyliminium cation species generated from o-alkynylbenzoic acid ester in the presence of a gold catalyst is highly reactive and underwent nucleophilic attack of various bulky alcohols and phenols at room temperature under neutral conditions, leading to the corresponding N,O-acetals in yields of 34-89% with good functional group tolerance.
NUCLEOSIDE PHOSPHONATE DERIVATIVES USEFUL IN THE TREATMENT OF HIV INFECTIONS
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Page/Page column 46, (2008/06/13)
The present invention relates to a method of treating HIV infections by administering a nucleoside phosphonate derivative represented by formula (I).
Inactivation of γ-Aminobutyric Acid Aminotransferase by (S,E)-4-Amino-5-fluoropent-2-enoic Acid and Effect on the Enzyme of (E)-3-(1-Aminocyclopropyl)-2-propenoic Acid
Silverman, Richard B.,Invergo, Benedict J.,Mathew, Jacob
, p. 1840 - 1846 (2007/10/02)
(S,E)-4-Amino-5-fluoropent-2-enoic acid (6) is synthesized in six steps starting from the known γ-aminobutyric acid aminotransferase (γ-Abu-T) inactivator, (S)-4-amino-5-fluoropentanoic acid (1).Compound 6 is a mechanism-based inactivator of γ-Abu-T: time-dependent inactivation is saturable and protected by substrate; thiols do not protect the enzyme from inactivation; no enzyme activity returns upon dialysis.This compound (6) binds 50 times more tightly to γ-Abu-T than does the saturated analogue (1).No transamination of 6 occurs prior to inactivation.However, five molecules of 6 are required to inactivate the enzyme with concomitant release of five fluoride ions.Therefore, four molecules are being converted to product for each inactivation event. (E)-3-(1-Aminocyclopropyl)-2-propenoic acid is synthesized in seven steps from 1-aminocyclopropanecarboxylic acid.It is prepared as a cyclopropyl derivative of the proposed intermediate in the inactivation of γ-Abu-T by 6.The cyclopropyl derivative, however, is a noncompetitive inhibitor and does not inactivate the enzyme.This study shows the usefulness and hazards of incorporation of a trans double bond into potential γ-Abu-T inactivators.
