69181-26-6

Usage

Uses

Used in Molecular Biology Research:
5-(((carboxymethyl)amino)methyl)uridine is used as a key molecule in molecular biology research for understanding the mechanisms of protein synthesis and the role of tRNA modifications in this process. The study of cmnm5U can provide insights into the regulation of gene expression and the development of potential therapeutic targets for various diseases.
Used in Pharmaceutical Development:
As a modification of tRNA, 5-(((carboxymethyl)amino)methyl)uridine holds potential in the development of novel pharmaceuticals targeting specific diseases. By modulating the activity of GidA and MnmE enzymes, it may be possible to develop drugs that can influence the levels of cmnm5U and, consequently, the regulation of protein synthesis. This could have implications for the treatment of various genetic disorders and other diseases associated with abnormal protein synthesis.
Used in Diagnostic Applications:
5-(((carboxymethyl)amino)methyl)uridine can also be employed in diagnostic applications to detect and monitor diseases related to abnormal protein synthesis. The measurement of cmnm5U levels in biological samples could serve as a biomarker for certain conditions, aiding in early diagnosis and treatment planning.

InChI:InChI=1/C12H17N3O8/c16-4-6-8(19)9(20)11(23-6)15-3-5(1-13-2-7(17)18)10(21)14-12(15)22/h3,6,8-9,11,13,16,19-20H,1-2,4H2,(H,17,18)(H,14,21,22)/t6-,8-,9-,11-/m1/s1

Upstream product

• 89129-08-8 5-<(N-trifluoroacetyl)methoxycarbonylmethylaminomethyl>uridine 
• 89845-85-2 {[1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl]-amino}-acetic acid tert-butyl ester 
• 3816-77-1 2',3'-O-isopropylidene-5-hydroxymethyl-uridine 
• 113790-35-5 Gly-tetra-n-butyl-ammonium salt 
• 78173-95-2 2-thio-5-<<(carboxymethyl)amino>methyl>uridine 
• 89129-06-6 Trifluoro-acetic acid (3aR,4R,6R,6aR)-6-(5-{[methoxycarbonylmethyl-(2,2,2-trifluoro-acetyl)-amino]-methyl}-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 89129-12-4 [[1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl]-(2,2,2-trifluoro-acetyl)-amino]-acetic acid tert-butyl ester 
• 89129-07-7 5--2',3'-O-isopropylidene uridine 
• 89129-04-4 2',3'-O-isopropylidene-5-<(N-benzyl)methoxycarbonylmethylaminomethyl>uridine 
• 89129-05-5 {[1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl]-amino}-acetic acid methyl ester 
• 89129-13-5 2',3'-O-isopropylidene-5-aminomethyluridine 
• 89148-09-4 5-chloromethyluridine 
• 72470-16-7 2',3'-O-isopropylidene-5-pyrrolidinomethyluridine 

Relevant academic research and scientific papers

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 influence of the C5 substituent on the 2-thiouridine desulfuration pathway and the conformational analysis of the resulting 4-pyrimidinone products

In recent years, increasing attention has been focused on the posttranscriptional modifications present in transfer RNAs (tRNAs), which have been suggested to constitute another level of regulation of gene expression. The most representative among them are the 5-substituted 2-thiouridines (R5S2U), which are located in the wobble position of the anticodon and play a fundamental role in the tuning of the translation process. On the other hand, sulfur-containing biomolecules are the primary site for the attack of reactive oxygen species (ROS). We have previously demonstrated that under in vitro conditions that mimic oxidative stress in the cell, the S2U alone or bound to an RNA chain undergoes desulfuration to yield uridine and 4-pyrimidinone nucleoside (H2U) products. The reaction is pH- and concentration-dependent. In this study, for the first time, we demonstrate that the substituent at the C5 position of the 2-thiouracil ring of R5S2Us influences the desulfuration pathway, and thus the products ratio. As the substituent R changes, the amount of R5H2U increases in the order H- > CH3O- > CH3OC(O)CH2- > HOC(O)CH2NHCH2- ≈ CH3NHCH2-, and this effect is more pronounced at lower pH. The conformational analysis of the resulting R5H2U products indicates that independent of the nature of the R5 substituent, the R5H2U nucleosides predominantly adopt a C2′-endo sugar ring conformation, as opposed to the preferred C3′-endo conformation of the parent R5S2Us.

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 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.