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PubMedDate not supplied

Mechanochemical degradation of aromatic sulfonic acids.

Sulfonic acids and sulfonates are widely used as surfactants in various industrial processes. Although partial biodegradation occurs, their release in the environment has determined a widespread pollution problem due to their remarkable tendency towards accumulation. For this reason, various methodologies to effectively degrade sulfonic acids and sulfonates in real matrices are currently under investigation. In this study, we focused our attention on the mechanochemical degradation of the 1,5-naphthalene disulfonic acid using strongly reducing agents such as pure Mg and Ca metals. The mechanochemical processing induced either a gradual degradation of the organic compound or a combustion-like reaction depending upon the experimental conditions. A partial degradation of the sulfonic acid was observed as a result of gradual reactions. An almost complete removal of the pollutant was instead observed after combustion-like reactions.

Calcium↗
PubMed1992

Alkyl phosphonic acids and sulfonic acids in the Murchison meteorite.

Homologous series of alkyl phosphonic acids and alkyl sulfonic acids, along with inorganic orthophosphate and sulfate, have been identified in water extracts of the Murchison meteorite after conversion to their t-butyl dimethylsilyl (tBDMS) derivatives. The methyl, ethyl, propyl, and butyl compounds have been observed in both series. Five of the eight possible alkyl phosphonic acids and seven of the eight possible alkyl sulfonic acids through C4 have been identified. Abundances decrease with increasing carbon number as observed of other homologous series indigenous to Murchison. Concentrations range downward from approximately 380 nmol/gram in alkyl sulfonic acid series, and from 9 nmol/gram in the alkyl phosphonic acid series. Inorganic phosphate is present at about 25 micromoles/gram.

Alkanesulfonic Acids↗
PubMed2006

Fragmentation of the deprotonated ions of peptides containing cysteine, cysteine sulfinic acid, cysteine sulfonic acid, aspartic acid, and glutamic acid.

We examined the fragmentation of the electrospray-produced [M-H]- and [M-2H]2- ions of a number of peptides containing two acidic amino acid residues, one being aspartic acid (Asp) or glutamic acid (Glu), and the other being cysteine sulfinic acid [C(SO2H)] or cysteine sulfonic acid [C(SO3H)], on an ion-trap mass spectrometer. We observed facile neutral losses of H2S and H2SO2 from the side chains of cysteine and C(SO2H), respectively, whereas the corresponding elimination of H2SO3 from the side chain of C(SO3H) was undetectable for most peptides that we investigated. In addition, the collisional activation of the [M-H]- ions of the C(SO2H)-containing peptides resulted in the cleavage of the amide bond on the C-terminal side of the C(SO2H) residue. Moreover, collisional activation of the [M-2H]2- ions of the above Asp-containing peptides led to the cleavage of the backbone N-Calpha bond of the Asp residue to give cn and/or its complementary [zn-H2O] ions. Similar cleavage also occurred for the singly deprotonated ions of the otherwise identical peptides with a C-terminal amide functionality, but not for the [M-H]- ions of same peptides with a free C-terminal carboxylic acid. Furthermore, ab initio calculation results for model cleavage reactions are consistent with the selective cleavage of the backbone N-Calpha bond in the Asp residue.

Amino Acid Sequence↗
PubMed1990

Initial steps in the degradation of benzene sulfonic acid, 4-toluene sulfonic acids, and orthanilic acid in Alcaligenes sp. strain O-1.

Alcaligenes sp. strain O-1 grew with benzene sulfonate (BS) as sole carbon source for growth with either NH4+ or NH4+ plus orthanilate (2-aminobenzene sulfonate, OS) as the source(s) of nitrogen. The intracellular desulfonative enzyme did not degrade 3- or 4-aminobenzene sulfonates in the medium, although the enzyme in cell extracts degraded these compounds. We deduce the presence of a selective permeability barrier to sulfonates and conclude that the first step in sulfonate metabolism is transport into the cell. Cell-free desulfonation of BS in standard reaction mixtures required 2 mol of O2 per mol. One mol of O2 was required for a catechol 2,3-dioxygenase. When meta ring cleavage was inhibited with 3-chlorocatechol in desalted extracts, about 1 mol each of O2 and of NAD(P)H per mol of BS were required for the reaction, and SO3(2-) and catechol were recovered in high yield. Catechol was shown to be formed by dioxygenation in an experiment involving 18O2. 4-Toluene sulfonate was subject to NAD(P)H-dependent dioxygenation to yield SO3(2-) and 4-methylcatechol, which was subject to meta cleavage. OS also required 2 mol of O2 per mol and NAD(P)H for degradation, and SO3(2-) and NH4+ were recovered quantitatively. Inhibition of ring cleavage with 3-chlorocatechol reduced the oxygen requirement to 1 mol per mol of OS SO3(2-) (1 mol) and an unidentified organic intermediate, but no NH4+, were observed.

Alcaligenes↗
PubMed2004

Fragmentation of protonated ions of peptides containing cysteine, cysteine sulfinic acid, and cysteine sulfonic acid.

The oxidation of the sulfhydryl group in cysteine to sulfenic acid, sulfinic acid, and sulfonic acid in proteins is important in a number of enzymatic processes. In this study we examined the fragmentation of four peptides containing cysteine, cysteine sulfinic acid (Cys-SO(2)H), and cysteine sulfonic acid (Cys-SO(3)H) in an ion-trap mass spectrometer. Our results show that the presence of a Cys-SO(2)H in a peptide leads to preferential cleavage of the amide bond at the C-terminal side of the oxidized cysteine residue. The results are important for the determination of the site of the cysteine oxidation and might be useful for the sequencing of cysteine-containing peptides.

Amino Acid Sequence↗
PubMed2005

Further studies on the fragmentation of protonated ions of peptides containing aspartic acid, glutamic acid, cysteine sulfinic acid, and cysteine sulfonic acid.

Here we examined the fragmentation, on a quadrupole ion-trap mass spectrometer, of the protonated ions of a group of peptides containing one arginine and two different acidic amino acids, one being aspartic acid (Asp) or glutamic acid (Glu) and the other being cysteine sulfinic acid [C(SO2H)] or cysteine sulfonic acid [C(SO3H)]. Our results showed that, upon collisional activation, the cleavage of the peptide bond C-terminal to C(SO2H) is much more facile than that of the peptide bond C-terminal to Asp, Glu, or C(SO3H). There is no significant difference, however, in susceptibility to cleavage of peptide bonds that are C-terminal to Asp, Glu, and C(SO3H). To understand these experimental observations, we carried out B3LYP/6-31G* density functional theory calculations for a model cleavage reaction of GXG --> b2 + Gly, in which X is Asp, Glu, C(SO2H), or C(SO3H). Our calculation results showed that the cleavage reaction is thermodynamically more favorable when X = C(SO2H) than when X = Asp or C(SO3H). We attributed the less facile cleavage of the amide bond after Glu to that the formation of a six-membered ring b ion for Glu-bearing peptides is kinetically not as favorable as the formation of a five-membered ring b ion for peptides containing the other three acidic amino acids. The results from this study may provide useful tools for peptide sequencing.

Amino Acid Sequence↗
PubMed2004

Blood compatibility of polyurethane immobilized with acrylic acid and plasma grafting sulfonic acid.

Sulfonic and carboxyl groups can effectively improve the blood compatibility of polyurethane. But it is difficult to obtain an optimum ratio of the two groups. In this article, polyurethane (PU) was dissolved with acrylic acid in a tetrahydrofuran solution and then spread on the glass plate to produce a film. At the same time, acrylic acid partly polymerized and immobilized with the PU films. The films (PU-AA) were exposed to sulfur dioxide plasma to graft sulfonic acid group on its surfaces. Through adjusting the quantity of acrylic acid and the plasma reaction condition, the antithrombin of polyurethane can be improved. The surface-modified PUs were characterized by attenuated total reflection Fourier transform infrared spectroscopy (ATR-FTIR), X-ray photoelectron spectroscope (XPS) and a contact angle goniometer. The blood compatibility of the films was examined by using thrombin time (TT), activated partial thromboplastin time (APTT) and prothrombin time (PT). The TT and APTT were significantly prolonged for the surface-modified films of PU-AA by sulfur dioxide plasma and only APTT was elongated for PU-AA. The results suggest that sulfonic acid and acrylic acid have the different effect on the blood compatibility of surface-modified PUs.

Acrylates↗
PubMed2006

Halichondria sulfonic acid, a new HIV-1 inhibitory guanidino-sulfonic acid, and halistanol sulfate isolated from the marine sponge Halichondria rugosa Ridley & Dendy.

A new sulfur-containing guanidino derivative, halichondria sulfonic acid (1) showing anti-HIV-1 activity, and halistanol trisulfate (2) with anti-tumor activity have been isolated from the marine sponge Halichondria rugosa Ridley & Dendy collected in the Chinese Southern Sea. The structure of 1 was elucidated by analysis of spectroscopic and crystal data.

Animals↗
PubMed2003

A general method for the synthesis of sugar 2-C-sulfonic acids by 1 --> 2 arylthio group migration in acid-sensitive thioglycosides. Direct transformation of thiotrityl ethers into C-sulfonic acids.

[reaction: see text] Fully protected triphenylmethyl 2-O-mesyl-1-thio-beta-d-gluco- (14) and -alpha-d-mannopyranoside (28) were transformed by a stereoselective intramolecular 1 --> 2 trans-arylthio migration into methyl 2-S-triphenylmethyl-alpha-d-manno- (15) and -beta-d-glucopyranoside (29), respectively, using NaOCH(3) as nucleophile. The 2-S-triphenylmethyl ethers (15 and 29) were directly oxidized to sugar 2-C-sulfonic acids by using oxone (2KHSO(5), KHSO(4), K(2)SO(4)). Compounds (21, 23, 32, and 35) are the first representatives of secondary sugar C-sulfonic acids.

Oxidation-Reduction↗
PubMed1978

Aminoalkane sulfonic acids. Synthesis of some mitodepressive heterocyclic aminoalkane sulfonic acids.

The reaction of 2-aminopyrimidine with benzaldehyde in all applied methods yielded instead of benzal-2-aminopyrimidine (1) regardless of the procedure used, N.N'-benzilidene-bis-2-aminopyrimidine (2). The expected product benzal-2-aminopyrimidine has not been formed in any case. For this reason the synthesis of aminoalkanesulfonic acids has not been carried out by the use of Schiff bases as starting material. Reaction of aldehyde bisulfite adducts and corresponding amine, was used instead. In the syntheses where 2-aminopyridine was used as the amine part, the corresponding aminoalkanesulfonic acids were formed (3--5), while 2-aminopyrimidine under the same condition gave several reaction products (6--10). All compounds obtained were tested for their growth inhibitory activity on the seeds of cress (Lepidium sativum L.).

Aminopyridines↗
PubMed2006

Determination of dopamine in the presence of ascorbic acid by poly(styrene sulfonic acid) sodium salt/single-wall carbon nanotube film modified glassy carbon electrode.

In this study, poly(styrene sulfonic acid) sodium salt/single-wall carbon nanotube film was cast onto the surface of glassy carbon electrode and the electrochemical behavior of the modified electrode was investigated. The results show that the anodic peak current is proportional to the concentration of dopamine in the range of 1.6 x 10(-8)-6 x 10(-4) M. The detection limit is 8 x 10(-9) M. The interference of ascorbic acid with the determination of dopamine could be eliminated due to the very distinct attracting interaction between dopamine cations and the negative poly(styrene sulfonic acid) sodium salt film in pH 7.0 phosphate-buffered saline solutions. The proposed method exhibits good sensitivity, selectivity, and reproducibility.

Ascorbic Acid↗