89998-90-3

Basic information

• Product Name: Uridine, 3'-carbamate
• CAS NO: 89998-90-3
• Molecular Formula: C10H13N3O7
• Molecular Weight: 287.229
• Mol File: 89998-90-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Uridine, 3'-carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine, 3'-carbamate(89998-90-3)
• EPA Substance Registry System: Uridine, 3'-carbamate(89998-90-3)

Safety Data

• Hazardous Substances Data: 89998-90-3(Hazardous Substances Data)

Usage

General Description

Uridine, 3'-carbamate is a chemically modified form of the nucleoside uridine, which is a component of RNA (ribonucleic acid) and plays a role in various biological processes. The 3'-carbamate modification involves the addition of a carbamate group to the 3' carbon of the ribose sugar in uridine. This modification is often used in the development of nucleoside analogs for potential therapeutic applications, particularly in the treatment of viral infections and cancer. Uridine, 3'-carbamate may exhibit altered pharmacokinetic and pharmacodynamic properties compared to unmodified uridine, making it a potential candidate for drug development and research in the field of nucleoside chemistry.

Upstream product

• 58-96-8 uridine 
• 28321-79-1 diiminosuccinonitrile 
• 506-68-3 bromocyane 
• 3106-18-1 uridine-5'-monophosphate sodium 

Relevant articles and documents

Reaction of Uridine and Uridine 5'-Phosphate with Diiminosuccinonitrile and Cyanogen Bromide in Aqueous Solution. Direct Synthesis of the 2,2'-Anhydronucleoside Linkage at 2 deg C

Reaction of uridine with diiminosuccinonitrile (DISN) at 2 deg C in aqueous solution yields 2,2'-anhydrouridine 3-carbamate (7) (54percent) along with 2,2'-anhydrouridine (8) (10percent), arabinofuranosyluracil (9) (9percent), uridine 2',3'-carbonate (10) (5percent), uridine 2'-carbamate (11) (3percent), and uridine 3'-carbamate (12) (9percent).A similar distribution of reaction products was obtained when BrCN was used in place of DISN.The same reaction products were isolated from the reaction of DISN or BrCN with uridine 5'-phosphate after the phosphate grouping was cleaved from the initial reaction product mixture with alkaline phosphatase.A reaction pathway is proposed in which the imidocarbonate derivative 6 is a common intermediate for product formation.The vicinal 2',3'-hydroxyl groups are essential for reaction as shown by the failure to form stable reaction products with thymidine (17).Adenosine (13), which has vicinal 2',3'-hydroxyl groups, is converted to a mixture of the 2'- and 3'-carbamates (15 and 16) via an imidocarbonate (14) intermediate with DISN or BrCN.The relevance of these studies to chemical evolution is discussed.