874-24-8Relevant articles and documents
In vitro reconstitution of the biosynthetic pathway of 3-hydroxypicolinic acid
Yun, Xuan,Zhang, Qian,Lv, Meinan,Deng, Hai,Deng, Zixin,Yu, Yi
, p. 454 - 460 (2019)
3-Hydroxypicolinic acid (3-HPA) is an important pyridine building block of bacterial secondary metabolites. Although the main biosynthetic pathways of these metabolites have been identified and well characterized, the enzymatic mechanism underlying the biosynthesis of 3-HPA has yet to be elucidated. In this work, we successfully reconstituted the complete biosynthetic pathway of 3-HPA in vitro. We showed that an l-lysine 2-aminotransferase, a two-component monooxygenase, and a FAD-dependent dehydrogenase are required to convert l-lysine to 3-HPA. We further demonstrated that 3-HPA does not derive from the direct hydroxylation of the picolinic acid at C-3, but from a successive process of C-3 hydroxylation of the piperideine-2-carboxylic acid and tautomerization of the produced 3-hydroxyl dihydropicolinic acid. Therefore, this study unveils the unusual assembly logic of 3-HPA and sheds light on the potential of engineering the 3-HPA pathway for generating novel pyridine-based building blocks.
Kinetics of oxidation of heterocyclic compounds by quinolinium dichromate
Saunte, Hauzachin,Chaubey, Girija S.,Mahanti, Mahendra K.
, p. 291 - 298 (2012/04/10)
Quinolinium dichromate in sulfuric acid oxidized heterocyclic aldehydes (to the corresponding acids) and heterocyclic carboxylic acids (to the corresponding hydroxy-substituted acids) in acetic acidwater medium (vol. ratio, v(water)/v(acetic acid) = 50:50). The kinetic results supported a mechanistic pathway proceeding via a rate-determining decomposition of the chromate ester.
3-Hydroxy-4-oxo-3,4-dihydro-5-azabenzo-1,2,3-triazene
Carpino, Louis A.,Xia, Jusong,El-Faham, Ayman
, p. 54 - 61 (2007/10/03)
The known but long-neglected compound HODhat was shown to be in certain situations a useful peptide coupling additive. Uronium and phosphonium salts with HODhat built into the system were also useful stand-alone coupling reagents. Comparisons with related additives and coupling reagents showed that the new systems were sometimes more and sometimes less effective than previously described systems in the case of stepwise and segment couplings. Applications to assembly of the model decapeptide ACP showed that HDATU was far more effective than HDTU and more effective than HATU under some conditions.