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.
Synthesis of phosphorus esters by transesterification mediated by N-heterocyclic carbenes (NHCs)
Singh, Rohit,Nolan, Steven P.
, p. 5456 - 5458 (2005)
The versatile nucleophilic organic catalysts N-heterocyclic carbenes (NHCs) have been shown to effectively mediate the transesterification of phosphorus esters under mild conditions; user-friendly imidazolium salts can also be employed as pre-catalysts. T
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
A modular approach for the installation of functionalized phosphonates to heterocycles
Shultz, Zachary,Shan, Chuan,Wojtas, Lukasz,Lopchuk, Justin M.
, p. 73 - 96 (2021/04/09)
Phosphonic acids and esters are pervasive throughout the discovery sciences, from medicine and agriculture, to materials and asymmetric synthesis. The ability to install and construct molecular architecture containing phosphonic functionality has led to 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.
Solid-Phase Synthesis of the Aged-Nonapeptide-Nerve-Agent Adduct of Butyrylcholinesterase as Reference Materials for Analytical Verification
Bielmann, Andreas,Curty, Christophe,Bochet, Christian G.
, (2017/12/01)
Two pathways were developed and investigated for the synthesis of the ‘aged’-nonapeptide nerve-agent bioadduct of human butyrylcholinesterase (BuChE). Considering the fast ageing of nerve-agent adducts of BuChE in patients and biomedical samples this target molecule is of paramount relevance for quantitative analysis with respect to the Chemical Weapons Convention. Two approaches using a precursor bearing a hydroxyl on its phosphonyl moiety and a benzyl protected precursor were considered. Several impurities were identified and circumvented during the optimization of the peptide synthesis step. The ‘aged’-nonapeptide adduct was successfully synthesized by solid-phase-peptide-synthesis (SPPS).
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.
Synthesis and biological evaluation of potential new inhibitors of the bacterial transferase MraY with a β-ketophosphonate structure
Auberger, Nicolas,Frlan, Rok,Al-Dabbagh, Bayan,Bouhss, Ahmed,Crouvoisier, Muriel,Gravier-Pelletier, Christine,Merrer, Yves Le
scheme or table, p. 8301 - 8312 (2012/04/23)
Stable analogs of bacterial transferase MraY substrate or product with a pyrophosphate surrogate in their structure are described. β- ketophosphonates were designed as pyrophosphate bioisosteres and were investigated as UDP-GlcNAc mimics. The developed st
Synthesis of a ss-ketophosphonate bioisostere of UDP-N- acetylglucosamine
Auberger, Nicolas,Gravier-Pelletier, Christine,Merrer, Yves Le
body text, p. 3323 - 3326 (2011/02/26)
A concise route to a new β-ketophosphonate analog of glycosyl nucleotides is described. Such a diphosphate bioisostere is a stable mimic of enzyme substrates involved, in peptidoglycan biosynthesis and will be the starting point for the development of new
P-Toluenesulfonic acid-Celite as a reagent for synthesis of esters of alkylphosphonic acids under solvent-free conditions
Gupta, Arvind K.,Kumar, Rajesh,Dubey, Devendra K.,Kaushik
, p. 328 - 331 (2008/02/10)
The coupling reaction of alkylphosphonic acids and alcohols on the surface of p-toluenesulfonic acid-Celite under mild and solvent-free conditions gave the corresponding phosphonates in excellent yields. This method provides a useful rapid synthesis of phosphonates for use in the unambiguous identification of chemical warfare agents.
