3968-19-2
Chemical Structure
(R)-Reticuline
- CAS No.: 3968-19-2
- Formula:C19H23NO4
- Molecular Weight:329.39
IUPAC Name: (R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
InChIKey: BHLYRWXGMIUIHG-OAHLLOKOSA-N
SMILES: OC1=CC2=C(C=C1OC)CCN(C)[C@@H]2CC3=CC=C(OC)C(O)=C3
Biological Activity: (R)-Reticuline is a key intermediate and precursor in the biosynthetic pathway of morphinan alkaloids. (R)-Reticuline plays a central role in the metabolism of opium poppy (Papaver somniferum). (R)-Reticuline can either undergo O-methylation catalyzed by PSOMT1, or be converted to (+)-Salutaridine via regioselective and stereoselective oxidative coupling under the action of salutaridine synthase (CYP719B1). (R)-Reticuline serves as a direct precursor for the synthesis of important alkaloids such as morphine, codeine and thebaine[1][2][3].
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(R)-Reticuline | (R)-Reticuline is a key intermediate and precursor in the biosynthetic pathway of morphinan alkaloids. (R)-Reticuline plays a central role in the metabolism of opium poppy (Papaver somniferum). (R)-Reticuline can either undergo O-methylation catalyzed by PSOMT1, or be converted to (+)-Salutaridine via regioselective and stereoselective oxidative coupling under the action of salutaridine synthase (CYP719B1). (R)-Reticuline serves as a direct precursor for the synthesis of important alkaloids such as morphine, codeine and thebaine. | |||||||||||||||||||||
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References
- [1]. Ounaroon A, et al. (R, S)‐Reticuline 7‐O‐methyltransferase and (R, S)‐norcoclaurine 6‐O‐methyltransferase of Papaver somniferum–cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy[J]. The plant journal, 2003, 36(6): 808-819.
- [2]. Gerardy R, et al. Formation of salutaridine from (R)-reticuline by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum[J]. Phytochemistry, 1992, 32(1): 79-86.
- [3]. Cigan E, et al. Concise synthesis of (R)-reticuline and (+)-salutaridine by combining early-stage organic synthesis and late-stage biocatalysis. Chem Sci. 2023;14(36):9863-9871. Published 2023 Aug 24. [Content Brief]
