78173-95-2

Basic information

• Product Name: 5-(carboxymethylaminomethyl)-2-thiouridine
• Synonyms: 5-(carboxymethylaminomethyl)-2-thiouridine
• CAS NO: 78173-95-2
• Molecular Formula: C12H17N3O7S
• Molecular Weight: 0
• Mol File: 78173-95-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.72g/cm³
• Refractive Index: 1.717
• CAS DataBase Reference: 5-(carboxymethylaminomethyl)-2-thiouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(carboxymethylaminomethyl)-2-thiouridine(78173-95-2)
• EPA Substance Registry System: 5-(carboxymethylaminomethyl)-2-thiouridine(78173-95-2)

Safety Data

• Hazardous Substances Data: 78173-95-2(Hazardous Substances Data)

Usage

Uses

5-Carboxymethylaminomethyl-2-thiouridine or mcm5S2U, is a naturally occurring 2-thio-modification of tRNA catalyzed by the action of Nfs1 enzyme on cy-tRNALyS2UUU and cy-tRNAGlU3UUC

Definition

ChEBI: A thiouridine that is 2-thiouridine bearing an additional carboxymethylaminomethyl substituent at position 5 on the thiouracil ring.

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 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 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.