55585-92-7

Basic information

• Product Name: N-acetyl-DL-homocysteine
• Synonyms: N-acetyl-DL-homocysteine
• CAS NO: 55585-92-7
• Molecular Formula: C₆H₁₁NO₃S
• Molecular Weight: 177.22144
• EINECS: 259-713-2
• Mol File: 55585-92-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 434.3°Cat760mmHg
• Flash Point: 216.5°C
• Appearance: /
• Density: 1.243g/cm³
• Vapor Pressure: 9.26E-09mmHg at 25°C
• Refractive Index: 1.513
• PKA: 3.50±0.10(Predicted)
• CAS DataBase Reference: N-acetyl-DL-homocysteine(CAS DataBase Reference)
• NIST Chemistry Reference: N-acetyl-DL-homocysteine(55585-92-7)
• EPA Substance Registry System: N-acetyl-DL-homocysteine(55585-92-7)

Safety Data

• Hazardous Substances Data: 55585-92-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H11NO3S/c1-4(8)7-5(2-3-11)6(9)10/h5,11H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1

Upstream product

• 348-67-4 D-methionine 
• 108-24-7 acetic anhydride 
• 41442-22-2 L-methionine sodium salt 
• 1195-16-0 N-acetyl-DL-homocysteinethiolactone 
• 5545-17-5 N,N'-bis(acetyl)cystine 

Downstream Products

• 348-67-4 D-methionine 
• 63-68-3 L-methionine 
• 1509-92-8 N-acetyl-D-methionine 
• 93428-83-2 N-acetyl-L-methionine anilide 

Relevant articles and documents

Mechanism-based inhibition of an essential bacterial adenine DNA methyltransferase: Rationally designed antibiotics [1]

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Rapid high-yield N-acylation of aminothiols: N-acetylglutathione and N-acetylhomocysteine and their thiol pKa values

Methodology for the rapid N-acylation of aminothiols in aqueous solution using procedures commonly employed in biochemical studies is described here. Glutathione disulfide (GSSG) and homocystine were diN-acetylated in ~100% yield in 0.1M aqueous NaHCO3 (pH 8.5) at room temperature by 2.5equiv of the activated ester, N-hydroxysulfosuccinimidyl acetate, an efficient water-soluble acetylating reagent. Following acetone precipitation, diN-acetylGSSG was further purified and desalted on a strong anion-exchange (SAX) cartridge. DiN-acetylhomocystine was simultaneously purified and desalted on a C18 cartridge. The N-acetylated aminothiols were generated using gel-immobilized tris(2-carboxyethyl)phosphine as a reductant, which obviated the need for further purification. Alternatively, disulfide exchange with dissolved dithiothreitol yielded N-acetylglutathione, which was purified on the SAX cartridge. pH titrations of N-acetylglutathione (8.99) and N-acetylhomocysteine (9.66) as well as those of commercially available N-acetylcysteine (9.53) and N-acetylpenicillamine (10.21) yielded pKa(SH) values of importance for biological studies.

DNA Methyltransferase inhibitors

A compound of the formula or a pharmaceutically acceptable salt thereof,whereinR1, R2, and R3 are the same or different and are independently hydrogen, lower alkyl, aryl or substituted aryl, lower alkoxy, lower alkoxyalkyl, or cycloalkyl or cycloalkyl alkoxy, where each cycloalkyl group has from 3-7 members, where up to two of the cycloalkyl members are optionally hetero atoms selected from oxygen and nitrogen, and where any member of the alkyl, aryl or cycloalkyl group is optionally substituted with halogen, lower alkyl or lower alkoxy, aryl or substituted aryl, andwhereR3 can be ribose, deoxyribose or phosphorylated derivatives thereof,whereinR1, R2, and R3 are not all hydrogen andwhereinwhen R3 is ribose, deoxyribose or phosphorylated derivatives thereof, one of R1 or R2 is not hydrogen.