2598-44-9

Basic information

• Product Name: S-(2-hydroxyethyl)homocysteine
• CAS NO: 2598-44-9
• Molecular Formula: C₆H₁₃NO₃S
• Molecular Weight: 179.2373
• Mol File: 2598-44-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 401.8°C at 760 mmHg
• Flash Point: 196.8°C
• Density: 1.301g/cm³
• Vapor Pressure: 3.98E-08mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: S-(2-hydroxyethyl)homocysteine(CAS DataBase Reference)
• NIST Chemistry Reference: S-(2-hydroxyethyl)homocysteine(2598-44-9)
• EPA Substance Registry System: S-(2-hydroxyethyl)homocysteine(2598-44-9)

Safety Data

• Hazardous Substances Data: 2598-44-9(Hazardous Substances Data)

Upstream product

• 764724-33-6 2-amino-4-mercapto-butyric acid methyl ester 
• 107-04-0 1-Bromo-2-chloroethane 
• 6027-13-0 L-homocysteine 
• 540-51-2 2-bromoethanol 
• 454-29-5 2-amino-4-mercaptobutyric acid 
• 1017-76-1 S-benzyl homocysteine 
• 861020-80-6 3,6-bis-[2-(2-hydroxy-ethylmercapto)-ethyl]-piperazine-2,5-dione 

Downstream Products

• 287408-84-8 methyl 2-({[4-(2-butynyloxy)phenyl]-sulfonyl}-amino)-4-[(2-hydroxyethyl)sulfanyl] butanoate 
• 287408-85-9 methyl 4-{[4-(2-butynyloxy)phenyl]sulfonyl}-1,4-thiazepine-5-carboxylate 
• 287408-86-0 4-{[4-(2-butynyloxy)phenyl]sulfonyl}-1,4-thiazepine-5-carboxylic acid 
• 287408-83-7 2-({[4-(2-butynyloxy)-phenyl]sulfonyl}amino)-4-[(2-hydroxyethyl)sulfanyl]butanoic acid 

Relevant articles and documents

Rationally engineered variants of S-adenosylmethionine (SAM) synthase: Reduced product inhibition and synthesis of artificial cofactor homologues

S-Adenosylmethionine (SAM) synthase was engineered for biocatalytic production of SAM and long-chain analogues by rational re-design. Substitution of two conserved isoleucine residues extended the substrate spectrum of the enzyme to artificial S-alkylhomocysteines. The variants proved to be beneficial in preparative synthesis of SAM (and analogues) due to a much reduced product inhibition. This journal is

ACETYLENIC ALPHA-AMINO ACID-BASED SULFONAMIDE HYDROXAMIC ACID TACE INHIBITORS

Compound of the formula (B) are useful in treating disease conditions mediated by TNF- alpha , such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.

Evidence for an episulfonium ion intermediate in the formation of S-[2-(N7-guanyl)ethyl]glutathione in DNA

The carcinogen ethylene dibromide (EDB) is bioactivated via a pathway involving initial conjugation with the tripeptide glutathione (GSH) in a reaction catalyzed by GSH S-transferase. The conjugate then reacts preferentially with DNA guanyl residues to generate S-[2-(N7-guanyl)ethyl]glutathione. Rates of hydrolysis and alkylation of 4-(p-nitrobenzyl)pyridine with several cysteinyl and homocysteinyl analogues of S-(2-haloethyl)glutathione at pHs 2.2, 6.4, and 8.5 are consistent with the hypothesis that an episulfonium ion is a common intermediate in both the hydrolysis and alkylation reactions. Consistently, 2-amino-6-chlorohexanoic acid failed to react with 4-(p-nitrobenzyl)pyridine. The stereochemical course of the overall reaction was studied with [threo-1,2-2H2]EDB and [erythro-1,2-2H2]EDB, which were incubated with GSH, rat liver cytosol, and DNA; the resulting DNA N7-guanyl adducts were isolated and analyzed by NMR techniques in order to determine the stereochemical course of the reaction. Two-dimensional correlated (COSY) NMR indicated that the reaction had occurred by a single stereochemical course. The magnitude of nuclear Overhauser effects between the ethylene protons suggests that the reaction occurs with net inversion of configuration of the methylene protons. This conclusion was confirmed upon comparison of the COSY NMR spectra of the biologically generated adducts with those that were synthetically prepared from the deuteriated EDB diastereomers via a known stereochemical route. This observation, combined with the kinetic data, supports a reaction mechanism where the EDB-GSH conjugate forms an episulfonium ion prior to reaction with DNA guanyl residues.