1206532-47-9

Upstream product

• 140438-71-7 tert-butyl (R)-4-((S)-1-hydroxybut-3-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 
• 100-39-0 benzyl bromide 
• 220317-60-2 1,1-dimethylethyl (4R)-(1'-hydroxy-3'-butenyl)-2,2-dimethyl-3-oxazolidinecarboxylate 
• 1206532-46-8 (R)-tert-butyl 4-[(S)-1-benzyloxybut-3-enyl]-2,2-dimethyloxazolidine-3-carboxylate 

Downstream Products

• 1206532-48-0 (2S,3S)-tert-butyl 3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)hex-5-enoate 

Relevant academic research and scientific papers

Synthesis of Deuterium-Labelled 3-Hydroxy- L -arginine: Comparative Studies on Different Protecting-Group Strategies

The β-hydroxy-α-amino acid 3-hydroxy-L-arginine is an important intermediate in biosynthetic pathways involving 2-oxoglutarate (2-OG) dependent FeII oxygenases. It also plays an essential role in post-translational modifications of ribosomal proteins. For profound studies on arginine-hydroxylating enzymes, synthetic reference compounds are of utmost importance. However, the synthesis of β-hydroxy-α-amino acids is often not trivial. In particular, the preparation of a densely functionalized compound such as 3-hydroxy-L-arginine poses a challenge in terms of a protecting-group strategy. We have previously established a concise synthesis of 3-hydroxy-L-arginine that is suitable for the preparation of both 3-epimers of this β-hydroxy-α-amino acid. However, we have since observed a remarkable isomerization reaction upon removal of the hydrogenolytically cleavable protecting groups, thus limiting the reliability of our previously described route. In this paper, we report a comparative study of protecting-group strategies for this synthetic route, including a newly developed, more robust pathway to the target amino acid. The versatility of this improved route is demonstrated by the synthesis of the deuterium-labelled derivatives (3R)- and (3S)-3-hydroxy-[5-2H]-L-arginine. These new isotope-labelled arginine derivatives represent important tools for the elucidation of biosynthetic pathways, such as the formation of the arginine-derived amino acid epicapreomycidine in the biosynthesis of muraymycin nucleoside antibiotics.

Concise synthesis of both diastereomers of 3-hydroxy-l-arginine

The hydroxylated amino acid 3-hydroxy-l-arginine is an intermediate in the biosynthesis of the non-proteinogenic amino acid capreomycidine and possibly also of its epimer epicapreomycidine. The novel concise synthesis of 3-hydroxy-l-arginine presented her