1236285-85-0

Basic information

• Product Name: 2,5-bis(4-hydroxybenzyl)pyrazine
• Synonyms: 2,5-bis(4-hydroxybenzyl)pyrazine
• CAS NO: 1236285-85-0
• Molecular Weight: 292.337
• Mol File: 1236285-85-0.mol

Chemical Properties

• CAS DataBase Reference: 2,5-bis(4-hydroxybenzyl)pyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-bis(4-hydroxybenzyl)pyrazine(1236285-85-0)
• EPA Substance Registry System: 2,5-bis(4-hydroxybenzyl)pyrazine(1236285-85-0)

Safety Data

• Hazardous Substances Data: 1236285-85-0(Hazardous Substances Data)

Upstream product

• 60-18-4 L-tyrosine 
• 153077-03-3 (S)-benzyl (1-(4-hydroxyphenyl)-3-oxopropan-2-yl)carbamate 
• 40829-66-1 (S)-2-(benzyloxycarbonylamino)-3-(4-hydroxyphenyl)-1-propanol 
• 13512-31-7 N-(benzyloxycarbonyl)-L-tyrosine methyl ester 

Relevant articles and documents

Preparation of new halogenated diphenyl pyrazine analogs in Escherichia coli by a mono-module fungal nonribosomal peptide synthetase from Penicillium herquei

Pyrazines are important structures widely found in many known drugs. The biological approaches for their synthesis were poorly applied. Herein, microbial production of several halogenated diphenyl pyrazines is reported. These compounds are accumulated via feeding corresponding precursor analogs to Escherichia coli expressing a fungal non-ribosomal peptide synthetase HqlA. Substrate specificity of HqlA was also determined by comparing substrate incorporation efficiencies. HqlA requires a C4-hydroxyl in the substrate and can tolerate certain degrees of size change on the substitution at the carbon next to the hydroxyl group.

Biosynthesis of Strained Piperazine Alkaloids: Uncovering the Concise Pathway of Herquline A

Nature synthesizes many strained natural products that have diverse biological activities. Uncovering these biosynthetic pathways may lead to biomimetic strategies for organic synthesis of such compounds. In this work, we elucidated the concise biosynthetic pathway of herquline A, a highly strained and reduced fungal piperazine alkaloid. The pathway builds on a nonribosomal peptide synthetase derived dityrosine piperazine intermediate. Following enzymatic reduction of the P450-cross-linked dicyclohexadienone, N-methylation of the piperazine serves as a trigger that leads to a cascade of stereoselective and nonenzymatic transformations. Computational analysis of key steps in the pathway rationalizes the observed reactivities.

A new method for the synthesis of symmetrical disubstituted pyrazines

Through the self-condensation of α-amino aldehydes, the synthesis of symmetrical disubstituted pyrazines was achieved in a three-step one-pot reaction. The α-amino aldehydes were easily obtained by treating methyl esters of natural α-amino acids with diisobutylaluminium hydride.

Pyrazine alkaloids via dimerization of amino acid-derived α-amino aldehydes: Biomimetic synthesis of 2,5-diisopropylpyrazine, 2,5-bis(3- indolylmethyl)pyrazine and actinopolymorphol C

The dimerization of amino acid-derived α-amino aldehydes provides a short, biomimetic synthesis of several 2,5-disubstituted pyrazine natural products. The α-amino aldehyde intermediates were generated in situ by the hydrogenolysis of their Cbz-derivative