32860-54-1

Basic information

• Product Name: 5-methylaminomethyl-2-thiouridine
• Synonyms: 5-methylaminomethyl-2-thiouridine;Uridine,5-[(methylamino)methyl]-2-thio-
• CAS NO: 32860-54-1
• Molecular Formula: C₁₁H₁₇N₃O₅S
• Molecular Weight: 303.33
• Mol File: 32860-54-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.58g/cm³
• Refractive Index: 1.691
• CAS DataBase Reference: 5-methylaminomethyl-2-thiouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methylaminomethyl-2-thiouridine(32860-54-1)
• EPA Substance Registry System: 5-methylaminomethyl-2-thiouridine(32860-54-1)

Safety Data

• Hazardous Substances Data: 32860-54-1(Hazardous Substances Data)

Usage

Description

5-methylaminomethyl-2-thiouridine, also known as m5s2U, is a modified nucleoside that is found in bacterial transfer RNA (tRNA) molecules. It is a wobble nucleoside, which means it plays a crucial role in the decoding of the genetic code during protein synthesis. The presence of this modified nucleoside in tRNAs specific for lysine (Lys) and glutamic acid (Glu) allows for more efficient and accurate translation of the genetic information into proteins.

Uses

Used in Molecular Biology and Genetics Research:
5-methylaminomethyl-2-thiouridine is used as a research tool for studying the structure and function of tRNA molecules, as well as the mechanisms of protein synthesis. Its presence in tRNAs specific for Lys and Glu makes it an important target for understanding the decoding process and the role of modified nucleosides in ensuring accurate translation of the genetic code.
Used in Drug Development:
The unique properties of 5-methylaminomethyl-2-thiouridine make it a potential target for the development of new drugs that could modulate protein synthesis. By targeting the interaction of this modified nucleoside with the ribosome or other components of the translation machinery, researchers may be able to develop novel therapeutics for various diseases, including those related to protein misfolding or aberrant protein synthesis.
Used in Biochemical and Structural Studies:
5-methylaminomethyl-2-thiouridine can be used as a probe in biochemical and structural studies to investigate the interactions between tRNA and other components of the translation machinery, such as ribosomes and aminoacyl-tRNA synthetases. This information can provide valuable insights into the molecular mechanisms underlying protein synthesis and the role of modified nucleosides in this process.
Used in Synthetic Biology:
The unique properties of 5-methylaminomethyl-2-thiouridine can also be exploited in the field of synthetic biology, where researchers engineer novel biological systems with specific functions. By incorporating this modified nucleoside into synthetic tRNAs or other RNA molecules, researchers can potentially create new ribosomes or other translation machinery components with altered or enhanced functions.
Used in Diagnostics:
5-methylaminomethyl-2-thiouridine could be used in the development of diagnostic tools for detecting specific tRNA modifications or monitoring the fidelity of protein synthesis in cells. By measuring the levels of this modified nucleoside in tRNAs, researchers may be able to gain insights into the cellular processes involved in protein synthesis and identify potential biomarkers for various diseases or conditions.

InChI:InChI=1/C11H17N3O5S/c1-12-2-5-3-14(11(20)13-9(5)18)10-8(17)7(16)6(4-15)19-10/h3,6-8,10,12,15-17H,2,4H2,1H3,(H,13,18,20)/t6-,7-,8-,10-/m1/s1

Upstream product

• 74-89-5 methylamine 
• 58479-71-3 5-hydroxymethyl-2',3'-O-isopropylidene-2-thiouridine 
• 54424-12-3 5-[(acetyl-methyl-amino)-methyl]-O^2',O^3',O^5'-tribenzoyl-5-methylaminomethyl-2-thio-uridine 
• 54424-11-2 methyl-(4-trimethylsilanyloxy-2-trimethylsilanylsulfanyl-pyrimidin-5-ylmethyl)-carbamic acid tert-butyl ester 
• 54424-10-1 N-methyl-N-(4-trimethylsilanyloxy-2-trimethylsilanylsulfanyl-pyrimidin-5-ylmethyl)-acetamide 
• 54424-09-8 5-(N-methyl-tert-butoxycarbonylamidomethyl)-2-thiouracil 
• 54424-08-7 5-(N-Methylacetamidomethyl)-2-thiouracil 
• 75921-11-8 5-methylaminomethyl-2-thiouracil trifluoroacetate 
• 75921-12-9 Methyl-trimethylsilanyl-(4-trimethylsilanyloxy-2-trimethylsilanylsulfanyl-pyrimidin-5-ylmethyl)-amine 
• 54424-07-6 Ethyl 3-propionate 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 54424-13-4 O^2'_,O3'_,O5'-tribenzoyl-5-methylaminomethyl-2-thio-uridine 
• 75921-10-7 N-[1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl]-N-methyl-acetamide 
• 89128-97-2 C₃₄H₂₈F₃N₃O₉S 

Downstream Products

• 72667-55-1 5-methylaminomethyluridine 

Relevant articles and documents

Synthesis of various substituted 5-methyluridines (xm5U) and 2-thiouridines (xm5s2U) via nucleophilic substitution of 5-pivaloyloxymethyluridine/2-thiouridine

5-Pivaloyloxymethyluridine and its 2-thio analogue have been utilized as convenient substrates for the synthesis of various 5-methyluridines (xm5U) and 5-methyl-2-thiouridines (xm5s2U). The pivaloyloxy group (OPiv) located at the pseudobenzylic position was effectively substituted with a series of nucleophiles: ammonia, primary and secondary amines including secondary cyclic amines, tetrabutylammonium salts of amino acids, an alkoxide and a thiolate.

THE PROTECTED DERIVATES OF 5-METHYLAMINOMETHYL-2-THIOURIDINE AND 5-CARBOMETHOXYMETHYL-2-THIOURIDINE AS COMPONENTS FOR THE OLIGONUCLEOTIDE SYNTHESIS

The syntheses of protected derivates of 5-methylaminomethyl-2-thiouridine(mnm5s2U) 11, 12 and 5-carbomethoxymethyl-2-thiouridine(mcm5s2U) 13 as well as their unprotected 3'-phosphates 14, 15 have been described.