n-[(9-beta-d-Ribofuranosyl-2-methylthiopurin-6-yl)carbamoyl]threonine

Base Information

• Chemical Name: n-[(9-beta-d-Ribofuranosyl-2-methylthiopurin-6-yl)carbamoyl]threonine
• CAS No.: 70333-82-3
• Molecular Formula: C₁₆H₂₂N₆O₈S
• Molecular Weight: 458.452
• DSSTox Substance ID: DTXSID30990541
• Nikkaji Number: J1.787.314H
• Wikidata: Q27109400
• Metabolomics Workbench ID: 53849
• Mol file: 70333-82-3.mol

Synonyms:N-((9-beta-D-ribofuranosyl-2-methylthiopurine-6-yl)carbamoyl)threonine;RMTPCT

Chemical Property of n-[(9-beta-d-Ribofuranosyl-2-methylthiopurin-6-yl)carbamoyl]threonine

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 1.85±0.10(Predicted)
• Flash Point: °C
• PSA: 240.97000
• Density: 1.91g/cm³
• LogP: -1.60740
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 458.12198285
• Heavy Atom Count: 31
• Complexity: 664

Purity/Quality:

97% ^*data from raw suppliers

2-Methylthio-N6-threonylcarbamoyladenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C(=O)O)NC(=O)NC1=C2C(=NC(=N1)SC)N(C=N2)C3C(C(C(O3)CO)O)O)O
• Isomeric SMILES: C[C@H]([C@@H](C(=O)O)NC(=O)NC1=C2C(=NC(=N1)SC)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)O
• Uses: 2-Methylthio-N6-threonylcarbamoyladenosine is a hypermodified form of Adenosine (A280400) found in bacterial and eukaryotic tRNAs at the A37 position adjacent to the 3’-end of the anticodon, which is essential for efficient and highly accurate protein translation by the ribosome.

Technology Process of n-[(9-beta-d-Ribofuranosyl-2-methylthiopurin-6-yl)carbamoyl]threonine

There total 26 articles about n-[(9-beta-d-Ribofuranosyl-2-methylthiopurin-6-yl)carbamoyl]threonine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

N-[[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-methylthiopurin-6-yl]carbamoyl]-L-threonine → 2-thiomethyl-L-N6-threonylcarbamoyladenosine (70333-82-3)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 5h;

DOI:10.1002/chem.201902411

Reference yield: 87.0%

2′,3′,5′-tri-O-acetyl-2-thiomethyl-D-allo-N6-threonylocarbamoyladenosine → 2-thiomethyl-D-allo-N6-threonylcarbamoyladenosine (70333-82-3)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 5h;

DOI:10.1002/chem.201902411

Reference yield:

C16H21N6O8S(1-)*C16H36N(1+) → 2-thiomethyl-L-N6-threonylcarbamoyladenosine (70333-82-3)

Guidance literature:

With calcium carbonate; In methanol; at 20 ℃; for 1h;

DOI:10.1039/d0ra09803e

upstream raw materials:

adenosine 1-oxide

2-(methylthio)adenosine

2′,3′,5′-tri-O-acetyl-2-methylthioadenosine

2',3',5'-tri-O-acetyl-guanosine

Refernces

• 1、 Debiec, Katarzyna,Matuszewski, Michal,Podskoczyj, Karolina,Leszczynska, Grazyna,Sochacka, Elzbieta. "Chemical Synthesis of Oligoribonucleotide (ASL of tRNALys T. brucei) Containing a Recently Discovered Cyclic Form of 2-Methylthio-N6-threonylcarbamoyladenosine (ms2ct6A)". . . Retrieved 2019/08/26.