463943-77-3

Upstream product

• 23316-67-8 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl-1-carbonitrile 
• 137272-74-3 1-amino-2,5-anhydro-3,4,6-tri-O-benzoyl-1-deoxy-D-allitol 
• 103-80-0 phenylacetyl chloride 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 

Downstream Products

• 463943-78-4 2,5-anhydro-1-deoxy-1-phenylacetamido-D-allitol 
• 463943-81-9 6-adenosine-diphosphate-2,5-anhydro-1-deoxy-1-phenylacetamido-D-allitol 
• 463943-79-5 2,5-anhydro-1-deoxy-1-phenylacetamido-D-allitol-6-phosphate 

Relevant academic research and scientific papers

Methylamine adenine dinucleotide (MAD): A co-factor to turn alcohol dehydrogenases into aldolases

Methylamine adenine dinucleotide (MAD) was prepared in seven steps and 15.3% overall yield from 1-acetoxy-2,3,5-tri-O-benzoyl-D-ribose by chemoenzymatic synthesis. The key step was the phosphate-phosphate coupling between adenosine monophosphate and 2,5-anhydro-1-deoxy-1-phenylacetamide-6-phosphate-D-allitol (3) mediated by carbonyl diimidazole (CDI), followed by the removal of the phenylacetamido group by penicillin G acylase. The MAD co-factor provided a primary amine functionality that was suitably positioned to promote the enamine aldolization of 2-oxopropionamide with aldehydes within the active site of alcohol dehydrogenases, which should lead to the transformation of these stereoselective enzymes into aldolases. Preliminary investigations did not reveal any activity with horse liver alcohol dehydrogenase or yeast alcohol dehydrogenase.