19236-58-9Relevant articles and documents
Isoprenoid biosynthesis via the MEP pathway. Synthesis of (3,4)-3,4-dihydroxy-5-oxohexylphosphonic acid, an isosteric analogue of 1-deoxy-D-xylulose 5-phosphate, the substrate of the 1-deoxy-D-xylulose 5-phosphate reducto-isomerase.
Meyer, Odile,Grosdemange-Billiard, Catherine,Tritsch, Denis,Rohmer, Michel
, p. 4367 - 4372 (2003)
(3,4)-3,4-Dihydroxy-5-oxohexylphosphonic acid, an isosteric analogue of 1-deoxy-D-xylulose 5-phosphate (DXP), was obtained in enantiomerically pure form from (+)-2,3--benzylidene--threitol by a seven-step sequence. This phosphonate did not affect the growth of. It did not inhibit the 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR), but was converted by this enzyme into (3,4)-3,4,5-trihydroxy-3-methylpentylphosphonic acid, an isosteric analogue of 2-C-methyl-D-erythritol 4-phosphate. The enzyme was, however, less efficient with the methylene phosphonate analogue than with the natural substrate.
N5-Phosphonoacetyl-l-ornithine (PALO): A convenient synthesis and investigation of influence on regulation of amino acid biosynthetic genes in Saccharomyces cerevisiae
Johnson, Brad,Steadman, Rachel,Patefield, Krista D.,Bunker, Jeffrey J.,Atkin, Audrey L.,Dussault, Patrick
, p. 2351 - 2353 (2011)
A scalable four-step synthesis of the ornithine transcarbamylase inhibitor N5-phosphonoacetyl-l-ornithine (PALO) is achieved through boroxazolidinone protection of ornithine. Investigations in the model organism Saccharomyces cerevisiae found t
Direct Catalytic Asymmetric Cyclopropylphosphonation Reactions of N,N-Dialkyl Groups of Aniline Derivatives by Ru(II)-Pheox Complex
Le, Chi Thi Loan,Ozaki, Seiya,Chanthamath, Soda,Shibatomi, Kazutaka,Iwasa, Seiji
supporting information, p. 4490 - 4494 (2018/08/07)
Novel catalysis involving phosphonomethylation of N-methylaniline and asymmetric cyclopropylphosphonation reactions of N,N-diethylaniline derivatives with diazomethylphosphonates are reported. Optically active cyclopropylphosphonate derivatives were directly synthesized from diazomethylphosphonates and N,N-diethylaniline derivatives catalyzed by a Ru(II)-Pheox complex in one step in good yields and high diastereoselectivities (up to trans/cis = > 99:1) and enantioselectivities (up to 99% ee). D-labeling mechanistic studies of phosphonomethylation and cyclopropylphosphonation suggested that an enamine or iminium intermediate was generated in the reaction process.
DBU-promoted alkylation of alkyl phosphinates and H-phosphonates
Gavara, Laurent,Petit, Christelle,Montchamp, Jean-Luc
supporting information, p. 5000 - 5003 (2012/11/07)
The alkylation of alkyl phosphinates and some H-phosphonate diesters is promoted by the base DBU. Only more reactive alkyl halides react in preparatively useful yields. However, the method provides easy access to important H-phosphinate building blocks, without the need for a protecting group strategy or metal catalysts. The reaction is conveniently conducted at, or below, room temperature. The preparation of methyl-H-phosphinate esters is particularly interesting as it avoids the heretofore more common use of methyldichlorophosphine MePCl2.
