2-mercaptoethanesulfonate

Sodium 2-mercaptoethanesulfonate (MESNA) [19767-45-4] M 164.2, pKj <0 (SOj ), pK 9.53 (SH). It can be recrystd from H2O and does not melt below 250°. It can be purified further by converting to the free acid by passing a 2M soln through an ion exchange (Amberlite IR-120) column in the acid form, evaporating the eluate in a vacuum to give the acid as a viscous oil (readily dec) which can be checked by acid and SH titration. It is then dissolved in H2O, carefully neutralised with aqueous NaOH, evaporated and recrystd from H2O [7 Am Chem Soc 77 6231 1955]. 

Allen JR, DD Clark, JG Krumn, SA Ensign (1999) A role for coenzyme M (2-mercaptoethanesulfonic acid) in a bacterial pathway of aliphatic epoxide carboxylation. Proc Natl Acad Sci USA 96 8432-8437. 

Krum JG, SA Ensign (2001) Evidence that a linear megaplasmid encodes enzymes of aliphatic alkene and epoxide metabolism and coenzyme M (2-mercaptoethanesulfonate) biosynthesis in Xanthobacter strain Py2. J Bacterial 183 2172-2177. 

ACE-I, angiotensin-converting enzyme inhibitor ADH, antidiuretic hormone (or vasopressin) ARB, angiotensin II receptor blocker, MESNA, sodium 2-mercaptoethanesulfonate TCA, tricyclic antidepressant Ul, urinary incontinence SUI, stress urinary incontinence UUI, urge urinary incontinence. 

Reconstruction of Au(lll) is observed in STM images as double rows separated from each other by 6.3 nm [335]. Some model calculations have been performed [362] to show that the energy difference of the reconstructed and unreconstructed Au(lll) is small. The effect of Triton X-100 on the reconstruction process of Au(lll) surface has been studied in chloride media [363] applying CV and double potential-step chronocoulometry. It has been found that adsorption of Triton X-100 stabilizes the reconstructed face of Au(lll). Hobara etal. [364] have used in situ STM to study reconstruction of Au(lll), following reductive desorption of 2-mercaptoethanesulfonic acid SAMs. 

Cysteic acid Sulphocysteine Phosphoserine Cysteine-2-mercaptoethanesulfonic acid disulfide... 

Zhou et al. studied the selective LbL assembly of NCs on microcontact printed carboxylate-functionalized SAMs.91 The LbL assembly was achieved by alternating adsorption of NCs functionalized with hydrophobic trioctylphosphine oxide and 2-mercaptoethanesulfonic acid, and positively charged linear poly(ethyleneimine) (LPEI). By adsorption of 11-mercaptoundecylhexa(ethylene glycol) in the noncon-tacted areas, nonspecific interactions were minimized. A uniform and linear growth of the polymer-NC layers was observed. 

SCHEME 11.6 Glycopeptide thioesterification via O-to-S acyl shift. MESNa, sodium 2-mercaptoethanesulfonate. 

The activity of sulfur towards platinum complexes has led to investigation of so-called rescue agents to ameliorate the side effects of platinum therapy, without compromising its anti-tumor activity. These nucleophilic sulfur compounds include sodium thiosulfate (STS), sodium diethyldithio-carbamate (Naddtc), (S)- 2-[(3-aminopropyl)amino]ethyl phosphorothioic acid (WR-2721, Ethyol , amifostine), glutathione (GSH), methionine, thiourea, cysteine, -acetylcysteine, penicillamine, biotin, sulfathiazole, sodium 2-mercaptoethanesulfonate (mesna), and its dimer (di)mesna (BNP-7787). The protective effect of these compounds is either due to prevention, or reversal of Pt-S adducts in proteins. Some of the more promising of the above-mentioned compounds (see Fig. 1) will be discussed below. 

Coenzyme M (CoM), 2-mercaptoethanesulfonic acid, was the first novel methanogen coenzyme described, and is the smallest organic coenzyme found in biological systems. The structure (Fig. 3) arose from work by Taylor, McBride, and Wolfe on methane production by extracts of Methanobacterium strain MOH, where a component was... 

MEK, 2-butanone, methyl ethyl ketone MEMO, 2-methoxyethoxymethylchloride Mercurochrome, mercury dibromofluorescein MES, 2-(7V-morpholino)-ethanesulfonic acid MESNA, Na 2-mercaptoethanesulfonate Metal impurities, by complexation by ion exchange resins by precipitation removal by extraction removal from reagents removal of lead removal of iron Methylarenes... 

Figure 2. Upper Gradient separation of o-phthalaldehyde derivatives of 11 thiols and sodium sulfite according to Mopper and Delmas Peaks (1) sodium sulfite (100 pmol) (2) glutathione (7 pmol) (3) thloglycollate (200 pmol) (4) N-acetylcysteine (7 pmol) (5) 2-mercaptoethanesulfonate (Co-M) (10 pmol) (6) 3-mercaptoproplonate (10 pmol) (8) monothloglycerol (10 pmol) (9) 2 mercaptoethanol (10 pmol) (10) methanethiol (15 pmol) (11) ethanethlol (10 pmol) (12) 2-propanethlol (15 pmol) (13) 1 propanethlol (15 pmol). Middle Thiols In porewater in reducing sediment slurry from Biscayne Bay. Porewater water was filter-sterilized prior to derlvatlzatlon. Peak 7 sulfide (Note response factor is about 200 times lower than for thiols). Lower reagent blank in porewater matrix.

Methylcobalamin also participates as a substrate for an enzymatic reaction in the formation of methane in certain methanogenic bacteria. In this reaction, which can be considered as a model for the second half-reaction of methionine synthetase, the cobalt-bound methyl group is transferred to 2-mercaptoethanesulfonic acid (coenzyme M) [39], the 5-methyl sulfide of which is subsequently reduced to yield methane. Additionally, methylcobalamin participates in the rather obscure process of acetate synthesis in certain bacteria in which it can be shown that the cobalt-bound methyl group becomes the acetate methyl carbon. The details of the involvement of methylcobalamin in this process are, however, unknown. 

Cyclophosphamide AI++, C+, D+, En+, G++, M++, R+ Hemodialysis effective. Acetylcysteine and 2-mercaptoethanesulfonate have been used investigationally to reduce hemorrhagic cystitis. 

---