78173-95-2

Usage

Uses

Used in Molecular Biology Research:
5-(carboxymethylaminomethyl)-2-thiouridine is used as a research tool for studying the role of tRNA modifications in various biological processes. Its presence in tRNA allows scientists to investigate the impact of these modifications on protein synthesis, gene expression, and other cellular functions.
Used in Drug Development:
As a naturally occurring tRNA modification, mcm5S2U has potential applications in drug development. Understanding its role in protein synthesis and cellular processes can lead to the discovery of new therapeutic targets and the development of drugs that modulate tRNA function to treat various diseases.
Used in Diagnostics:
The presence of 5-(carboxymethylaminomethyl)-2-thiouridine in tRNA can also be utilized in diagnostic applications. Detection and analysis of mcm5S2U levels in biological samples can provide valuable information about the health of an individual and the presence of certain diseases or conditions.
Used in Biochemistry Education:
mcm5S2U serves as an important example of post-transcriptional modifications in tRNA. It can be used in biochemistry education to teach students about the complexity of RNA biology, the role of modifications in RNA function, and the importance of understanding these processes in the context of cellular function and disease.

InChI:InChI=1/C12H17N3O7S/c16-4-6-8(19)9(20)11(22-6)15-3-5(1-13-2-7(17)18)10(21)14-12(15)23/h3,6,8-9,11,13,16,19-20H,1-2,4H2,(H,17,18)(H,14,21,23)/t6-,8-,9-,11-/m1/s1

Upstream product

• 113790-35-5 Gly-tetra-n-butyl-ammonium salt 
• 58479-71-3 5-hydroxymethyl-2',3'-O-isopropylidene-2-thiouridine 
• 89129-10-2 [[1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl]-(2,2,2-trifluoro-acetyl)-amino]-acetic acid tert-butyl ester 
• 58479-74-6 2',3'-O-isopropylidene-5-chloromethyl-2-thiouridine 
• 89845-82-9 2',3'-O-isopropylidene-5-pyrrolidinomethyl-2-thiouridine 
• 6984-55-0 2',3'-O-isopropylidene-2-thiouridine 
• 89129-11-3 5-<(N-trifluoroacetyl)methoxycarbonylmethylaminomethyl>-2-thiouridine 
• 89129-09-9 {[1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl]-amino}-acetic acid tert-butyl ester 
• 89129-07-7 5--2',3'-O-isopropylidene uridine 

Downstream Products

• 69181-26-6 5-carboxymethylaminomethyluridine 

Relevant academic research and scientific papers

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.

Chemistry and structure of modified uridines in the anticodon, wobble position of transfer RNA are determined by thiolation

Uridines found in the first or wobble position of transfer RNA anticodons are most often modified at base ring carbon-5 and many times also thiolated at carbon-2. It is important to understand the chemistry and structure of the modified uridines because t

The Synthesis of 5-Carboxymethylaminomethyluridine and 5-Carboxymethylaminomethyl-2-thiouridine

2',3'-O-Isopropylideneuridine (1a) and 2',3'-O-isopropylidene-2-thiouridine (1b) are converted in 4 steps, via the corresponding Mannich bases (2a) and (2b), into the modified nucleosides (5a) and (5b), respectively.

THE MODIFIED NUCLEOSIDES FROM THE " WOBBLE POSITION " OF tRNAs. THE SYNTHESIS OF 5-CARBOXYMETHYLAMINOMETHYLURIDINE AND 5-CARBOXYMETHYLAMINOMETHYL-2-THIOURIDINE

The synthesis of 5-carboxymethylaminomethyluridine isolated from tRNA1Gly(B. subtilis) and its 2-thio analogue from tRNALys(B. subtilis) have been described.