122699-13-2

Basic information

• Product Name: 5-BroMo-2',3',5'-tri-O-t-butyldiMethylsilyluridine
• Synonyms: 5-BroMo-2',3',5'-tri-O-t-butyldiMethylsilyluridine
• CAS NO: 122699-13-2
• Molecular Formula: C23H41BrN2O6Si
• Molecular Weight: 549.57094
• Mol File: 122699-13-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-BroMo-2',3',5'-tri-O-t-butyldiMethylsilyluridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BroMo-2',3',5'-tri-O-t-butyldiMethylsilyluridine(122699-13-2)
• EPA Substance Registry System: 5-BroMo-2',3',5'-tri-O-t-butyldiMethylsilyluridine(122699-13-2)

Safety Data

• Hazardous Substances Data: 122699-13-2(Hazardous Substances Data)

Upstream product

• 58-96-8 uridine 
• 957-75-5 5-bromouridine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 64898-15-3 2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine 

Relevant articles and documents

Lys314 is a nucleophile in non-classical reactions of orotidine-5′- monophosphate decarboxylase

Orotidine-5′-monophosphate decarboxylase (OMPD) catalyzes the decarboxylation of orotidine-5′-monophosphate (OMP) to uridine-5′-monophosphate (UMP) in an extremely proficient manner. The reaction does not require any cofactors and proceeds by an unknown mechanism. In addition to decarboxylation, OMPD is able to catalyze other reactions. We show that several C6-substituted UMP derivatives undergo hydrolysis or substitution reactions that depend on a lysine residue (Lys314) in the OMPD active site. 6-Cyano-UMP is converted to UMP, and UMP derivatives with good leaving groups inhibit OMPD by a suicide mechanism in which Lys314 covalently binds to the substrate. These non-classical reactivities of human OMPD were characterized by cocrystallization and freeze-trapping experiments with wildtype OMPD and two active-site mutants by using substrate and inhibitor nucleotides. The structures show that the C6-substituents are not coplanar with the pyrimidine ring. The extent of this substrate distortion is a function of the substituent geometry. Structurebased mechanisms for the reaction of 6-substituted UMP derivatives are extracted in accordance with results from mutagenesis, mass spectrometry, and OMPD enzyme activity. The Lys314based mechanisms explain the chemodiversity of OMPD, and offer a strategy to design mechanism-based inhibitors that could be used for antineoplastic purposes for example.

ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF

The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.

Alternative nucleic acid molecules and uses thereof

The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.

ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF

The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.

MODIFIED NUCLEIC ACID MOLECULES AND USES THEREOF

The present disclosure provides modified nucleosides, nucleotides, and nucleic acids, and methods of using them.

Study on the synthesis of 6-alkylaminouridines via the nucleophilic aromatic substitution reaction of 6-cyanouridine derivatives

6-Cyanouracil derivatives underwent direct substitution reactions with selective primary amines in the presence of N,N-dimethylaminopyridine as a catalyst to give the corresponding 6-alkylaminouracils. This reaction provides a facile access to versatile 6

The AlkB domain of mammalian ABH8 catalyzes hydroxylation of 5-methoxycarbonylmethyluridine at the wobble position of tRNA

Family ties: The AlkB family of nonheme iron, α-ketoglutarate (αKG)-dependent dioxygenases is involved in biological processes such as DNA/RNA repair and obesity. The AlkB domain of ABH8 is shown to catalyze the hydroxylation of a modified uridine (mcmsu

In-cell Indirect Electrochemical Halogenation of Pyrimidine Bases and their Nucleosides to 5-Haloderivatives

Reaction of anodically generated "halonium" species (LiX or Bu4NX, LiClO4, MeCN, Pt/Pt; I2, LiClO4, MeCN) with pyrimidine bases and their nucleosides leads to 5-halo compounds in good yields.