1190-93-8

Usage

Chemical Properties

Light Yellow Oil

InChI:InChI=1/C4H6O3S/c1-3(5)8-2-4(6)7/h2H2,1H3,(H,6,7)

Upstream product

• 68-11-1 mercaptoacetic acid 
• 75-36-5 acetyl chloride 
• 507-09-5 thioacetic acid 
• 79-11-8 chloroacetic acid 
• 6398-67-0 S-Acetyl-thioglykolsaeure-trimethylsilylester 
• 507-09-5 tiolacetic acid 
• 108-24-7 acetic anhydride 
• 79-08-3 bromoacetic acid 
• 830-03-5 4-nitrophenol acetate 

Downstream Products

• 1456-72-0 2-methyl-5-phenyl-1,3,4-thiadiazole 
• 10553-78-3 (acetylthio)acetyl chloride 
• 169319-37-3 (S)-2-{[1-(2-Acetylsulfanyl-acetylamino)-cyclopentanecarbonyl]-amino}-3-(4-hydroxy-phenyl)-propionic acid methyl ester 
• 76931-93-6 N-succinimidyl-S-acetylthioacetate 
• 1188931-96-5 S-2-((R)-4-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis(tert-butyldimethylsilyloxy)cyclohexylidene)ethylidene)-7a-methyl-octahydro-7H-inden-1-yl)pentylamino)-2-oxoethyl ethanethioate 
• 1445651-90-0 S-(2-((5-((tert-butoxycarbonyl)amino)pentyl)amino)-2-oxoethyl) ethanethioate 
• 68-11-1 mercaptoacetic acid 

Relevant academic research and scientific papers

Gold Nanoparticles Decorated with Sialic Acid Terminated Bi-antennary N-Glycans for the Detection of Influenza Virus at Nanomolar Concentrations

Gold nanoparticles decorated with full-length sialic acid terminated complex bi-antennary N-glycans, synthesized with glycans isolated from egg yolk, were used as a sensor for the detection of both recombinant hemagglutinin (HA) and whole influenza A virus particles of the H1N1 subtype. Nanoparticle aggregation was induced by interaction between the sialic acid termini of the glycans attached to gold and the multivalent sialic acid binding sites of HA. Both dynamic light scattering (DLS) and UV/Vis spectroscopy demonstrated the efficiency of the sensor, which could detect viral HA at nanomolar concentrations and revealed a linear relationship between the extent of nanoparticle aggregation and the concentration of HA. UV/Vis studies also showed that these nanoparticles can selectively detect an influenza A virus strain that preferentially binds sialic acid terminated glycans with α(2→6) linkages over a strain that prefers glycans with terminal α(2→3)-linked sialic acids.

Mechanism-based inhibition of 5-aminolaevulinic acid dehydratase from Bacillus subtilis by the 3-thia analogue of the substrate

The interaction of various substrate analogues with 5-aminolaevulinic acid dehydratase (porphobilinogen synthase) from Bacillus subtilis is studied kinetically and by electrospray mass spectrometry; 5-chlorolaevulinic acid is shown to be a non-specific alkylating agent but 5-amino-3-thialaevulinic acid is a potent mechanism-based inactivator.

Design, Synthesis, and Antifungal Activities of 3-Acyl Thiotetronic Acid Derivatives: New Fatty Acid Synthase Inhibitors

Emerging fungal phytodiseases are increasingly becoming a food security threat. Twenty-six new 3-acylthiotetronic acid derivatives were designed, synthesized, characterized, and evaluated for activities against Valsa Mali, Curvularia lunata, Fusarium graminearum, and Fusarium oxysporum f. sp. lycopersici. Among the 26 compounds, 6f was the most effective against V. Mali, C. lunata, F. graminearum, and F. oxysporum f. sp. lycopersici with median effective concentrations (EC50) of 4.1, 3.1, 3.6, and 4.1 μg/mL, respectively, while the corresponding EC50 were 0.14, 6.7, 22.4, and 4.3 μg/mL of the fungicide azoxystrobin; 4.2, 41.7, 0.42, and 0.12 μg/mL of the fungicide carbendazim; and >50, 0.19, 0.43, and BS > 50 μg/mL of the fungicide fluopyram. The inhibitory potency against V. Mali fatty acid synthase agreed well with the in vitro antifungal activity. The molecular docking suggested that the 3-acylthiotetronic acid derivatives targeted the C171Q KasA complex. The findings help understanding the mode of action and design and synthesis of novel potent fungicides.

Design, synthesis, and in vitro and biological evaluation of potent amino acid-derived thiol inhibitors of the metallo-β-lactamase IMP-1

There are currently no clinically available inhibitors of metallo-β-lactamases (MBLs). These enzymes confer resistance to bacteria against a broad range of commonly used β-lactam antibiotics, and are produced by an increasing number of bacterial pathogens. In this study, several thiol derivatives of l-amino acids were designed and synthesized, and their inhibitory effects against the metallo-β-lactamase IMP-1 (subclass B1) were investigated. The most potent compound, derived from l-tyrosine, exhibited competitive inhibition, with a Ki of 86 nM. The ability of this compound to render MBL-expressing bacteria susceptible to imipenem was examined. Reductions in MIC values up to 5.2 - fold were observed.

Gold Nanoparticles Decorated with Sialic Acid Terminated Bi-antennary N-Glycans for the Detection of Influenza Virus at Nanomolar Concentrations

Gold nanoparticles decorated with full-length sialic acid terminated complex bi-antennary N-glycans, synthesized with glycans isolated from egg yolk, were used as a sensor for the detection of both recombinant hemagglutinin (HA) and whole influenza A virus particles of the H1N1 subtype. Nanoparticle aggregation was induced by interaction between the sialic acid termini of the glycans attached to gold and the multivalent sialic acid binding sites of HA. Both dynamic light scattering (DLS) and UV/Vis spectroscopy demonstrated the efficiency of the sensor, which could detect viral HA at nanomolar concentrations and revealed a linear relationship between the extent of nanoparticle aggregation and the concentration of HA. UV/Vis studies also showed that these nanoparticles can selectively detect an influenza A virus strain that preferentially binds sialic acid terminated glycans with α(2→6) linkages over a strain that prefers glycans with terminal α(2→3)-linked sialic acids.

Synthesis of α,α-difluoro-β-amino esters or gem-difluoro-β-lactams as potential metallocarboxypeptidase inhibitors

The synthesis of gem-difluorinated β-lactams and gem-difluorinated β-amino acids, each possessing a potential basic functional group, from ethyl bromodifluoroacetate and either imines (for β-lactams) or N-(α-aminoalkyl)benzotriazoles (for β-amino esters) was investigated. A series of these compounds were used for the design of novel metallocarboxypeptidase inhibitors. N-Alkylation and N-acylation of these two versatile scaffolds were carried out, leading to the expected targets in moderate to good yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Thiol-based angiotensin-converting enzyme 2 inhibitors: P1 modifications for the exploration of the S1 subsite

Screening of a metalloprotease library led to the identification of a thiol-based dual ACE/NEP inhibitor as a potent ACE2 inhibitor. Modifications of the P1 benzyl moiety led to improvements in ACE2 potency as well as to increased selectivity versus ACE and NEP.

Transition state stabilization by micelles: Thiolysis of p-nitrophenyl alkanoates in cetyltrimethylammonium bromide micelles

Thiolysis of p-nitrophenyl esters (acetate to decanoate) by the anion of 2-mercaptoethanol (ME) is catalyzed by micelles of cetyltrimethylammonium bromide (CTAB) in aqueous solution. At fixed [ME], the observed rate constants (k(obs)) show saturation with

Synthesis of analogues of 5-aminolaevulinic acid and inhibition of 5-aminolaevulinic acid dehydratase

Syntheses are described of several analogues of 5-aminolaevulinic acid (ALA), which are potential inhibitors of ALA dehydratase (porphobilinogen synthase), an early enzyme of tetrapyrrole biosynthesis.Most of the analogues are relatively weak competitive inhibitors of the enzyme from Bacillus subtilis or irreversible inhibitors due to multiple alkylation of the enzyme but the 3-oxa and 3-thia analogues are potent mechanism-based inhibitors which inactive, by acylation of a nucleophilic residue, probably the active-site lysine residue.The kinetics of the inactivation by 3-thiaALA have implications for the mechanism of the enzymic reaction.

4H-Thieno[3,4-c]pyrazole derivatives with antiinflammatory, analgesic, antipyretic and platelet antiaggregating activities

The synthesis of a series of 1-aryl-1,6-dihydro-4H-thieno[3,4-c)pyrazol-4-ones by cyclization of 3-[(2-arylhydrazino)methylene]thiophene-2,4(3H,5H)-diones, prepared by reacting 3-dimethylaminomethylenethiophene-2,4(3H,5H)-dione with arylhydrazines, is described. The 4-fluorophenyl derivative showed remarkable analgesic, antiinflammatory and antipyretic activities in mice or rats, as well as a platelet antiaggregating activity in vitro comparable to that of acetylsalicylic acid.