5796-14-5

Usage

InChI:InChI=1/C9H11NO4.ClH/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5;/h1-2,4,6,11-12H,3,10H2,(H,13,14);1H/t6-;/m0./s1

Upstream product

• 59-92-7 levodopa 
• 139-85-5 3,4-dihydroxybenzaldehyde 

Downstream Products

• 137018-93-0 N-(9-fluorenylmethyloxycarbonyl)-3,4-dihydroxy-L-phenylalanine 
• 881911-33-7 (S)-3-(3,4-bis-trityloxy-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid 

Relevant academic research and scientific papers

Synthesis of a Photo-Caged DOPA Derivative by Selective Alkylation of 3,4-Dihydroxybenzaldehyde

Natural and synthetic polymers containing the catechol moiety of noncoded amino acid 3,4-dihydroxyphenylalanine (DOPA) are capable of metal-coordination and adhesion under wet conditions. Masking the catechol subunit with a photo-cleavable group would provide an opportunity to design tunable adhesion properties that are especially important for biomaterial and biomedicine applications. Herein, we report the regioselective synthesis of a photo-caged DOPA bearing an ortho-nitrobenzyl (oNB) group that is capable of undergoing cleavage upon irradiation with UV light. We developed a selective synthetic route towards a 3-O-oNB alkylated DOPA regioisomer that can be readily incorporated into proteins by using a previously developed bio-expression platform. The synthesis is based on a regioselectivity switch in 3,4-dihydrozybenzaldehyde alkylation upon application of different equivalents of deprotonating base. The enantiomerically pure 3-O-oNB-DOPA was prepared on a gram scale and proved to be generally compatible with the solid-phase peptide synthesis conditions. We also demonstrate the general applicability of the developed synthetic strategy by providing the synthesis of 3-O-methyl-DOPA.

LEVODOPA DIMETHYL-SUBSTITUTED DIESTER PRODRUGS, COMPOSITIONS, AND METHODS OF USE

Levodopa dimethyl-substituted diester prodrugs, pharmaceutical, compositions comprising levodopa dimethyl-substituted diester prodrugs, and methods of using such prodrugs and pharmaceutical compositions for treating diseases such as Parkinson's disease are provided. Formula (I)

NOVEL HYDROCHLORIDE SALTS OF LEVODOPA

The present invention provides a novel hydrochloride salt of levodopa. In addition, pharmaceutical compositions comprising said hydrochloride salt of levodopa may be used as fast-dissolve compositions. Methods of making and of using the same are also provided.