21691-49-6

Basic information

• Product Name: D-METHIONINE METHYL ESTER
• Synonyms: D-METHIONINE METHYL ESTER;(2R)-2-Amino-4-(methylthio)butanoic acid methyl ester;(R)-2-Amino-4-(methylthio)butanoic acid methyl ester;(R)-Methionine methyl ester;O-Methyl-D-methionine;UIHPNZDZCOEZEN-RXMQYKEDSA-N
• CAS NO: 21691-49-6
• Molecular Formula: C₆H₁₃NO₂S
• Molecular Weight: 163.23792
• Mol File: 21691-49-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 240℃
• Flash Point: 99℃
• Appearance: /
• Density: 1.094
• CAS DataBase Reference: D-METHIONINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: D-METHIONINE METHYL ESTER(21691-49-6)
• EPA Substance Registry System: D-METHIONINE METHYL ESTER(21691-49-6)

Safety Data

• Hazardous Substances Data: 21691-49-6(Hazardous Substances Data)

Usage

General Description

D-Methionine methyl ester is a chemical compound with the formula C6H13NO2S. It is a derivative of the amino acid methionine and is commonly used as a building block in the synthesis of peptides and proteins. D-METHIONINE METHYL ESTER is known for its ability to serve as a precursor for the production of S-adenosyl methionine, a key molecule involved in numerous biochemical processes in the body. D-Methionine methyl ester has also been studied for its potential therapeutic effects in the treatment of liver diseases and as a protective agent against oxidative stress. Additionally, it has been investigated for its potential as an ingredient in dietary supplements, particularly those aimed at improving liver function and overall health.

Upstream product

• 67-56-1 methanol 
• 348-67-4 D-methionine 
• 77-76-9 2,2-dimethoxy-propane 
• 74-88-4 methyl iodide 
• 10332-17-9 DL-methionine methyl ester 
• 87-69-4 L-Tartaric acid 

Downstream Products

• 22838-79-5 (S)-3-Benzyloxycarbonylamino-N-((R)-1-methoxycarbonyl-3-methylsulfanyl-propyl)-succinamic acid benzyl ester 
• 140647-67-2 N-9-fluorenylmethyloxycarbonyl-DL-3,3-difluoro-phenylalanyl-L-methionyl methyl ester 
• 155102-63-9 methyl (2R)-2-(benzyloxycarbonylamino)-4-methylthiobutyrate 
• 69630-60-0 methyl D-methioninate hydrochloride 
• 10420-68-5 N-(2,4-Dinitro-phenyl)-methionin-methylester 
• 1581267-11-9 (2S,6R,9S,12R,13S)-12-[(S)-isobutyl]-13-(tert-butyldimethylsilyloxy)-6-[2-(methylthio)ethyl]-2-[(E)-4-(tritylthio)but-1-en-1-yl]-9-tritylthiomethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone 
• 1581266-97-8 (3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]-4-(methylthio)butanoylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate 
• 1581266-95-6 (R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enamide]-4-(methylthio)butanoic acid 
• 1581266-93-4 methyl (R)-2-{(S,E)-3-[(4-methoxybenzyl)oxy]-7-(tritylthio)hept-4-enamido}-4-(methylthio)butanoate 
• 1191249-23-6 (R)-methyl 2-(3-(4-chlorophenyl)-4-cyano-5-(isopropylthio)thiophene-2-carboxamido)-4-(methylthio)butanoate 
• 247568-83-8 N-(3,4-dimethoxylbenzyl)-2-[(R)-1-methoxycarbonyl-3-(methylthio)propylamino]-5-nitrobenzamide 
• 383661-95-8 N-[[(3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]-D-methionine methyl ester 
• 1509-92-8 N-acetyl-D-methionine 

Relevant articles and documents

Enantioselective friedel-crafts alkylation of pyrrole with chalcones catalyzed by a dinuclear zinc catalyst

A highly enantioselective Friedel-Crafts (F-C) alkylation of pyrrole with a wide range of simple nonchelating chalcone derivatives catalyzed by a chiral (Zn2EtL)n (L = (S,S)-1) complex has been developed. The catalyst (Zn2EtL)n complex was prepared in situ by reacting the chiral ligand (S,S)-1 with 2 equiv of diethylzinc. A series of β-pyrrole-substituted dihydrochalcones were usually formed mostly in excellent yields (up to 99%) and excellent enantioselectivity [up to 99% enantiomeric excess (ee)] by using 15 mol % catalyst loading under mild conditions. The absolute stereochemistry of the products was determined to be the S-configuration by X-ray crystallographic analysis of 13g. Meanwhile, a weak negative nonlinear effect was observed. On the basis of the experimental results and previous reports, a possible mechanism was proposed to explain the origin of the asymmetric induction.

Crystallographic studies on the reaction of isopenicillin N synthase with an unsaturated substrate analogue

Isopenicillin N synthase (IPNS) catalyses conversion of the linear tripeptie δ-(L-α-aminoadipoyl)-L-cysteinyl-D-valine (ACV) to isopenicillin N (IPN), the central step in biosynthesis of the β-lactam antibiotics. The unsaturated substrate analogue δ-(L-α-aminoadipoyl)-L-cysteinyl-D-vinylglycine (ACvG) has previously been incubated with IPNS and a single product was isolated, a 2-α-hydroxymethyl isopenicillin N (HMPen), formed via a monooxygenase mode of reactivity. ACvG has now been crystallised with IPNS and the structure of the anaerobic IPNS:Fe(II):ACvG complex determined to 1.15 A resolution. Furthermore, by exposing the anaerobically grown crystals to high-pressure oxygen gas, a structure corresponding to the bicyclic product HMPen has been obtained at 1.60 A resolution. In light of these and other IPNS structures, and recent developments with related dioxygenases, the [2 + 2] cycloaddition mechanism for HMPen formation from ACvG has been revised, and a stepwise radical mechanism is proposed. This revised mechanism remains consistent with the observed stereospecificity of the transformation, but fits better with apparent constraints on the coordination geometry around the active site iron atom.

Potential application of Sulfolobus solfataricus as catalyst in organic synthesis

Sulfolobus solfataricus, a thermoacidophilic archaeon, has been utilized as catalyst for several enzymatic transformations such as carbonyl-alcohol oxidoreductions, synthesis of glycosides, kinetic resolution of aminoacid esters, etc.All these reactions have been carried out at 75 deg C in accordance with the thermophilic nature of the enzymes present in the organisms.