136-09-4

Basic information

• Product Name: 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazoniol-5-yl]ethyl dihydrogen diphosphate
• Synonyms: 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazoniol-5-yl]ethyl dihydrogen diphosphate;3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-5-[2-(phosphonooxyoxylatophosphinyloxy)ethyl]thiazol-3-ium
• CAS NO: 136-09-4
• Molecular Formula: C16H24N4O8P2S
• Molecular Weight: 494.396282
• EINECS: 205-230-7
• Mol File: 136-09-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Water Solubility: 77g/L at 20℃
• CAS DataBase Reference: 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazoniol-5-yl]ethyl dihydrogen diphosphate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazoniol-5-yl]ethyl dihydrogen diphosphate(136-09-4)
• EPA Substance Registry System: 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazoniol-5-yl]ethyl dihydrogen diphosphate(136-09-4)

Safety Data

• Hazardous Substances Data: 136-09-4(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

Purification Methods

Cocarboxylase tetrahydrate recrystallises from aqueous Me2CO. [Wenz et al. Justus Liebigs Ann Chem 618 210 1958, UV: Melnick J Biol Chem 131 615 1939, X-ray: Carlisle & Cook Acta Cryst (B) 25 1359 1969.] The hydrochloride salt has m 242-244o(dec), 241-243o(dec) or 239-240o(dec) and crystallises from aqueous HCl/EtOH, EtOH containing HCl or HCl/Me2CO. [Weijlard J Am Chem Soc 63 1160 1941, Synthesis: Weijlard & Tauber J Am Chem Soc 60 2263 1938, Beilstein 27 III/IV 1777.]

InChI:InChI=1/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)

Synthetic route

Aneurin (70-16-6) → thiamine pyrophosphate (136-09-4)

Conditions	Yield
With thiamin pyrophosphokinase; ATP; magnesium chloride In water at 20℃; for 12h; pH=8;	75%

5-hydroxyethyl-4-methylthiazole (137-00-8) + 2-methyl-4-amino-5-hydroxymethylpyrimidine (73-67-6) → thiamine pyrophosphate (136-09-4)

Conditions	Yield
With HMP-pyrimidine kinase; thiamin phosphate synthase; thiazole kinase; thiamin phosphate kinase; ATP In water at 20℃; for 12h; pH=8;	71%

thiamine pyrophosphate (136-09-4) + methyl sodium acetyl phosphonate (69103-75-9) → 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-2-[1-hydroxy-1-(hydroxy-methoxy-phosphoryl)-ethyl]-4-methyl-5-(2-trihydroxydiphosphoryloxy-ethyl)-thiazolium betaine (72040-70-1)

Conditions	Yield
In water

1-oxopropylphosphinic acid (325775-28-8) + thiamine pyrophosphate (136-09-4) → C15H25N4O10P3S

Conditions	Yield
With glyoxylate carboligase I393A variant; potassium chloride; flavin adenine dinucleotide; magnesium chloride In aq. phosphate buffer at 37℃; pH=7.7; Enzymatic reaction;

sodium glyoxylate (2706-75-4) + thiamine pyrophosphate (136-09-4) → C14H19N4O10P2S(1-)*Na(1+)

Conditions	Yield
With glyoxylate carboligase I393A variant; flavin adenine dinucleotide; magnesium chloride In aq. phosphate buffer at 37℃; pH=7.7; Enzymatic reaction;

acetylphosphinate (50654-76-7) + thiamine pyrophosphate (136-09-4) → C14H23N4O10P3S

Conditions	Yield
With glyoxylate carboligase I393A variant; flavin adenine dinucleotide; magnesium chloride In aq. phosphate buffer at 37℃; pH=7.7; Enzymatic reaction;

methyl hydrogen acetylphosphonate (63502-77-2) + thiamine pyrophosphate (136-09-4) → C15H25N4O11P3S

Conditions	Yield
With glyoxylate carboligase I393A variant; potassium chloride; flavin adenine dinucleotide; magnesium chloride In aq. phosphate buffer at 37℃; pH=7.7; Enzymatic reaction;

sodium pyruvate (113-24-6) + thiamine pyrophosphate (136-09-4) → C15H21N4O10P2S(1-)*Na(1+)

Conditions	Yield
With glyoxylate carboligase I393A variant; potassium chloride; flavin adenine dinucleotide; magnesium chloride In aq. phosphate buffer at 37℃; pH=7.7; Reagent/catalyst; Enzymatic reaction;

Upstream product

• 137-00-8 5-hydroxyethyl-4-methylthiazole 
• 73-67-6 2-methyl-4-amino-5-hydroxymethylpyrimidine 
• 67-03-8 Thiamine hydrochloride 
• 70-16-6 Aneurin 

Downstream Products

• 154-87-0 thiamine diphosphate 

Relevant articles and documents

An efficient enzymatic synthesis of thiamin pyrophosphate

Thiamin pyrophosphate was synthesized in 71% yield, on a multi-milligram scale, using overexpressed thiazole kinase, pyrimidine kinase, thiamin phosphate synthase, and thiamin phosphate kinase. This provides a facile route to isotopically labeled thiamin pyrophosphate from its readily available pyrimidine and thiazole precursors.