4105-39-9

Basic information

• Product Name: 2-methylthioadenosine
• Synonyms: 2-Methylthioadenosine ( 2-MeS-Ado )
• CAS NO: 4105-39-9
• Molecular Formula: C₁₁H₁₅N₅O₄S
• Molecular Weight: 313.3329
• Mol File: 4105-39-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 747.6°Cat760mmHg
• Flash Point: 406°C
• Appearance: /
• Density: 1.98g/cm³
• Vapor Pressure: 1.77E-23mmHg at 25°C
• Refractive Index: 1.878
• CAS DataBase Reference: 2-methylthioadenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methylthioadenosine(4105-39-9)
• EPA Substance Registry System: 2-methylthioadenosine(4105-39-9)

Safety Data

• Hazardous Substances Data: 4105-39-9(Hazardous Substances Data)

Usage

General Description

2-Methylthioadenosine, also known as MTA, is a naturally occurring chemical compound that is derived from Adenosine, a nucleoside that plays essential roles in biochemical processes like protein synthesis and cellular communication. Known for its sulfur-containing species, MTA is known to influence various biological processes such as cell growth, differentiation, and apoptosis, predominantly via polyamine synthesis pathway or methionine salvage pathway, where it serves as a precursor. Therefore, alterations in MTA metabolism are often linked to several pathological conditions, including cancer and neurological disorders. Due to its biological significance, 2-methylthioadenosine has been the subject of various research studies aiming to elucidate its roles in human health and disease.

InChI:InChI=1/C11H15N5O4S/c1-21-11-14-8(12)5-9(15-11)16(3-13-5)10-7(19)6(18)4(2-17)20-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)

Upstream product

• 1198-83-0 2-(methylthio)-7H-purin-6-amine 
• 105499-44-3 2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride 
• 146-77-0 2-Chloroadenosine 
• 5188-07-8 sodium thiomethoxide 
• 70255-65-1 2′,3′,5′-tri-O-acetyl-2-methylthioadenosine 
• 51549-17-8 2',3',5'-tri-O-benzoyl-2-(methylthio)adenosine 
• 43157-50-2 2-Mercaptoadenosine 
• 74-88-4 methyl iodide 
• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 1198-83-0 2-methylthio-6-aminopurine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 16321-99-6 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 35109-88-7 2-iodoadenosine 
• 94042-04-3 6-amino-2-iodo-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine 

Downstream Products

• 22140-20-1 2-methylthioadenosine 5'-monophosphate 
• 445417-49-2 phenyl N-[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamate 
• 445417-51-6 N-[[9-(β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester 
• 445417-50-5 N-[[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester 
• 445417-52-7 N-[[9-(5'-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester 
• 445417-53-8 N-[[9-(2'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester 
• 122970-32-5 2',3'-Dideoxy-2-(methylthio)adenosine 
• 13406-51-4 2-methylthio-N⁶-methyladenosine 
• 70333-82-3 2-thiomethyl-L-N⁶-threonylcarbamoyladenosine 
• 70333-82-3 2-thiomethyl-D-allo-N⁶-threonylcarbamoyladenosine 

Relevant articles and documents

An RNA complex of the HIV-1 A-loop and tRNALys,3 is stabilized by nucleoside modifications

The HIV transcription initiation complex involves a putative interaction between the primer tRNA anticodon and a conserved A-rich loop in the HIV genome. Surface plasmon resonance was used to demonstrate that the hypermodified nucleosides in the tRNA anti

Chemical Synthesis of Oligoribonucleotide (ASL of tRNALys T. brucei) Containing a Recently Discovered Cyclic Form of 2-Methylthio-N6-threonylcarbamoyladenosine (ms2ct6A)

The synthesis of the protected form of 2-methylthio-N6-threonylcarbamoyl adenosine (ms2t6A) was developed starting from adenosine or guanosine by using the optimized carbamate method and, for the first time, an isocyanate route. The hypermodified nucleoside was subsequently transformed into the protected ms2t6A-phosphoramidite monomer and used in a large-scale synthesis of the precursor 17nt ms2t6A-oligonucleotide (the anticodon stem and loop fragment of tRNALys from T. brucei). Finally, stereochemically secure ms2t6A→ms2ct6A cyclization at the oligonucleotide level efficiently afforded a tRNA fragment bearing the ms2ct6A unit. The applied post-synthetic approach provides two sequentially homologous ms2t6A- and ms2ct6A-oligonucleotides that are suitable for further comparative structure–activity relationship studies.

New highly active antiplatelet agents with dual specificity for platelet P2Y1 and P2Y12 adenosine diphosphate receptors

Currently approved platelet adenosine diphosphate (ADP) receptor antagonists target only the platelet P2Y12 receptor. Moreover, especially in patients with acute coronary syndromes, there is a strong need for rapidly acting and reversible antiplatelet agents in order to minimize the risk of thrombotic events and bleeding complications. In this study, a series of new P1,P4-di(adenosine-5′) tetraphosphate (Ap4A) derivatives with modifications in the base and in the tetraphosphate chain were synthesized and evaluated with respect to their effects on platelet aggregation and function of the platelet P2Y1, P2Y12, and P2X1 receptors. The resulting structure-activity relationships were used to design Ap4A analogs which inhibit human platelet aggregation by simultaneously antagonizing both P2Y1 and P2Y12 platelet receptors. Unlike Ap4A, the analogs do not activate platelet P2X1 receptors. Furthermore, the new compounds exhibit fast onset and offset of action and are significantly more stable than Ap4A to degradation in plasma, thus presenting a new promising class of antiplatelet agents.

NOVEL ANTITHROMBOTIC DIADENOSINE TETRAPHOSPHATES AND RELATED ANALOGS

The invention features compounds of formula I and methods of their use as antiplatelet and antithrombotic compounds: H /N=Qχ2 O O O O Λ Q2 — N, H R6/ N I f ) ( ^ XM O-Mγτ OM°τ X1MQ' ) r ( ^rf HO OH HO OQHi Nχi R2 Formula (I).