101669-78-7Relevant articles and documents
The design and synthesis of inhibitors of dethiobiotin synthetase as potential herbicides
Rendina,Taylor,Gibson,Lorimer,Rayner,Lockett,Kranis,Wexler,Marcovici-Mizrahi,Nudelman,Nudelman,Marsilii,Chi,Wawrzak,Calabrese,Huang,Jia,Schneider,Lindqvist,Yang
, p. 236 - 247 (1999)
Dethiobiotin synthetase (DTBS; E.C. 6.6.6.6), the penultimate enzyme in the biosynthesis of the essential vitamin biotin, is a new potential target for novel herbicides. Inhibitors were designed based on mechanistic and structural information. The in-vitro activities of these potential inhibitors versus the bacterial enzyme are reported here. Mimics of 7,8- diaminopelargonic acid (DAPA) or the DAPA carbamate reaction intermediate were substrates or partial substrates for the enzyme. Synergistic binding with ATP was noted with compounds which contained an amino functionality. NMR studies and X-ray structures confirmed that the inhibitors could be phosphorylated by the enzyme. Several series of potential inhibitors were designed to take advantage of this partial substrate activity by generating potentially more tightly bound phosphorylated inhibitors in situ. Structure- activity relationships for these series based on both substrate and inhibitory activity are described herein. An X-ray structure for one of these inhibitors is also discussed. Although considerable potential for inhibitors of this type was demonstrated, none of the compounds reported showed sufficient herbicidal activity to be a commercial proposition.
The synthesis of the vitamers of biotin
Nudelman, Abraham,Nudelman, Ayelet,Marcovici-Mizrahi, Dana,Flint, Dennis
, p. 157 - 168 (2007/10/03)
An efficient synthetic pathway for the preparation of the vitamers of biotin which provides easy access to optically pure KAPA as well as diastereomeric mixtures of DAPA, DTB, and analogs thereof has been developed.
Decarboxylative Carbon Acylation of Malonates with Aminoacylimidazoles Mediated by Lewis Acids
Mansour, Tarek S.,Evans, Colleen A.
, p. 773 - 781 (2007/10/02)
Various N-protected aminoacylimidazoles undergo decarboxylative carbon acylation with sodium or potassium monomethylmalonate in THF in the presence of MgCl2, CoCl2 or MnCl2 to give dipeptide analogues (3) in 45-82percent isolated yield.Amino ketoester (3e) undergoes intramolecular cyclization induced by diisopropylethylamine and anhydrous magnesium chloride to trisubstituted tetramic acid (4).
