2812-40-0

Basic information

• Product Name: N,N-α-dimethyl-L-tryptophan
• Synonyms: N,N-α-dimethyl-L-tryptophan
• CAS NO: 2812-40-0
• Molecular Weight: 232.282
• Mol File: 2812-40-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N,N-α-dimethyl-L-tryptophan(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-α-dimethyl-L-tryptophan(2812-40-0)
• EPA Substance Registry System: N,N-α-dimethyl-L-tryptophan(2812-40-0)

Safety Data

• Hazardous Substances Data: 2812-40-0(Hazardous Substances Data)

Upstream product

• 485-80-3 S-adenosyl-L-methionine 
• 73-22-3 L-Tryptophan 

Relevant articles and documents

Iterative l-Tryptophan Methylation in Psilocybe Evolved by Subdomain Duplication

Psilocybe mushrooms are best known for their l-tryptophan-derived psychotropic alkaloid psilocybin. Dimethylation of norbaeocystin, the precursor of psilocybin, by the enzyme PsiM is a critical step during the biosynthesis of psilocybin. However, the “magic” mushroom Psilocybe serbica also mono- and dimethylates l-tryptophan, which is incompatible with the specificity of PsiM. Here, a second methyltransferase, TrpM, was identified and functionally characterized. Mono- and dimethylation activity on l-tryptophan was reconstituted in vitro, whereas tryptamine was rejected as a substrate. Therefore, we describe a second l-tryptophan-dependent pathway in Psilocybe that is not part of the biosynthesis of psilocybin. TrpM is unrelated to PsiM but originates from a retained ancient duplication event of a portion of the egtDB gene that encodes an ergothioneine biosynthesis enzyme. During mushroom evolution, this duplicated gene was widely lost but re-evolved sporadically and independently in various genera. We propose a new secondary metabolism evolvability mechanism, in which weakly selected genes are retained through preservation in a widely distributed, conserved pathway.