208655-84-9

Usage

Uses

Used in Pharmaceutical Industry:
Uridine, 2',3'-diacetate 5'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite] is used as a reagent for the biosynthesis of C-glycosidic UDP-GlcNAc analogs. These analogs serve as substrate-based inhibitors for UDP-GlcNAc 2-epimerase, an enzyme that plays a crucial role in the biosynthesis of carbohydrates. By inhibiting this enzyme, the compound can potentially be used in the development of therapeutic strategies targeting carbohydrate-related metabolic pathways and diseases.

Upstream product

• 111426-09-6 1-[2',3'-di-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-β-D-ribo-pentofuranosyl]-uracil 
• 102691-36-1 N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite 
• 29108-90-5 2',3'-di-O-acetyl-uridine 
• 124482-92-4 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine 

Downstream Products

• 208655-85-0 (S)-3-(4-{(2-Cyano-ethoxy)-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid allyl ester 
• 537677-39-7 (S)-3-(4-{(2-Cyano-ethoxy)-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (2-chloro-phenyl)-diphenyl-methyl ester 
• 537677-37-5 2-cyanoethyl-N^α-(9-fluorenylmethoxycarbonyl)tyrosin-4-yl-(2',3'-di-O-acetyluridin-5'-yl)phosphate 

Relevant academic research and scientific papers

Phosphorus deprotonation by a non-nucleophilic base is critical for the synthesis of nucleoside α-P-boranodiphosphates via a phosphoramidite approach

Here we report the synthesis of nucleoside α-P-boranodiphosphate analogs via our improved phosphoramidite approach, where the addition of a non-nucleophilic base, TEA, to deprotonate phosphorus is considered to be critical to improve final product yields. Protonation on trivalent phosphorus might not only have blocked Lewis acid borane modification, but also have promoted byproduct formation through a trans-nucleophile process. Here, based on 31P NMR data, mechanisms are proposed for P(V)P(III) bond cleavage via phosphorus protonation-promoted nucleophile-exchange, and TEA deprotonation of phosphorus in promoting product formation in anhydrous synthetic reaction mixtures.

UDP-GlcNAc Analogues as Inhibitors of O-GlcNAc Transferase (OGT): Spectroscopic, Computational, and Biological Studies

A series of glycomimetics of UDP-GlcNAc, in which the β-phosphate has been replaced by either an alkyl chain or a triazolyl ring and the sugar moiety has been replaced by a pyrrolidine ring, has been synthesized by the application of different click-chemistry procedures. Their affinities for human O-GlcNAc transferase (hOGT) have been evaluated and studied both spectroscopically and computationally. The binding epitopes of the best ligands have been determined in solution by means of saturation transfer difference (STD) NMR spectroscopy. Experimental, spectroscopic, and computational results are in agreement, pointing out the essential role of the binding of β-phosphate. We have found that the loss of interactions from the β-phosphate can be counterbalanced by the presence of hydrophobic groups at a pyrroline ring acting as a surrogate of the carbohydrate unit. Two of the prepared glycomimetics show inhibition at a micromolar level.

Synthesis of sugar nucleotides by application of phosphoramidites

(Chemical Equation Presented) A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate-phosphite intermediate was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.

C-glycosidic UDP-GlcNAc analogues as inhibitors of UDP-GlcNAc 2-epimerase

The first step in the biosynthesis of neuraminic acid, the "epimerisation" of UDP-GlcNAc to ManNAc, is catalyzed by UDP-GlcNAc 2-epimerase. In this paper we report the synthesis of the C-glycosidic UDP-GlcNAc analogues 1-5 as substrate-based inhibitors of this enzyme. The focus is on the optimal distance and geometry of the connection between the sugar and the UDP-moiety, which are both important for recognition by UDP-GlcNAc 2-epimerase. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Stepwise solid phase synthesis of uridylylated viral genome-linked peptides using uridylylated amino acid building blocks

The uridylylated amino acid building blocks 2-cyanoethyl-(Nα-9-fluorenylmethoxy-carbonyl-tyrosin-4-yl)- (2′,3′-di-O-acetyluridin-5′-yl) phosphate and 2-chlorophenyl-(Nα-fluorenyl-methoxycarbonyl-serin-3-yl)- (2′,3′-di-O-acetyluridin-5′-yl) phosphate have been used successfully in an on-line SPPS of the VPgpU from the polio, coxsackie and cowpea mosaic virus.