Myronic acid

Another glycoside belonging in the same category as sinalbin is sinigrin, which is the potassium salt of a complex acid, myronic acid. It... 

I-Thio-ft-D-glucopyranose 7-/N-(sulfooxy )-3-butenimidate ], 9CI. Sinigrin. Allyl glucosinolate. Myronic acid [534-69-0]... 

Brassica alba (L.) Rabenh. B. juncea (L.) Czem. et Coss. Bai Jie Zi (Indian mustard) (seed, young shoot) Sinigrin, myrocin, sinapic acid, sinapine, potassium myronate, mustard oil, allyl isothiocyanate, behenic acid, erucic acid, benzyl isothiocyanate, eicosenic acid.48-50 Relieve bladder inflammation, hemorrhage, abscesses, lumbago, rheumatism, stomach disorders. 

A Golan-Goldhirsh, DT Osuga, AO Chen, JR Whitaker. Effect of ascorbic acid and copper on proteins. In VT D Souza, J Feder, eds. The Bioorganic Chemistry of Enzymatic Catalysis An Eiomage to Myron L. Bender. Boca Raton, FL CRC Press, 1992, pp 61-76. 

We have made several artificial enzymes that use cyclodextrin to bind a substrate and then react with it by acylating a cyclodextrin hydroxyl group. This builds on earlier work by Myron Bender, who first studied such acylations [83]. We added groups to the cyclodextrin that produced a flexible floor, capping the ring [84]. The result was to increase the relative rate of cyclodextrin acylation by m-t-butylphenyl acetate from 365 relative to its hydrolysis rate in the buffer to a Complex/ buffer of 3300. We changed the substrate to achieve better geometry for the intracomplex acylation reaction, and with a p-nitrophenyl ester of ferroceneacrylic acid 10 we achieved a relative rate for intracomplex acylation of ordinary [3-cyclodextrin vs. hydrolysis of over 50 000 and a Vmax comparable to that for hydrolysis of p-nitrophenyl acetate by chymotrypsin... 

Spring Grove Hospital, 33 Stafford collection, 15 Stafford, Peter, 44 Stark, Ron, 87 Steinberg, Saul, 87 Steindl-Rast, David, 84 stereoisomers, 66 Stevens, Jay, 60 stimulant properties, 41 Stolaroff, Myron, 15,20 Storming Heaven LSD and the American Dream, 60 Stormy Search for the Self, 29 stress reduction, 68,71,76,81 striychnine, 50 strippers, 62 Sudafed, 66 suicide, 76,78,82 Sunshine acid, 87 sweating, 69 synapses, 48 synergies, 48,86 synthesis of MDMA, 86 synthetic psychedelics, 44,50 Syrian rue, 43... 

The most important species in the mechanism for ester hydrolysis is the tetrahedral intermediate. Evidence in support of the existence of the tetrahedral intermediate was developed by Professor Myron Bender on the basis of isotopic labeling experiments he carried out at the University of Chicago. Bender prepared ethyl benzoate, labeled with the mass-18 isotope of oxygen at the carbonyl oxygen, then subjected it to acid-catalyzed hydrolysis in ordinary (unlabeled) water. He found that ethyl benzoate, recovered from the reaction before hydrolysis was complete, had lost a portion of its isotopic label. This observation is consistent only with the reversible formation of a tetrahedral intermediate under the reaction conditions ... 

At temperatures above 40° (104° F.) myrosin becomes coagulated and incapable of decomposing potassium myronate, a. change which is also produced by contact with acetic acid. Aa the rubefacient and vesicant actions of mustard when moistened with HaO, are due to the prod action of allyl sulfocyanate, neither-vinegar, acetic acid, nor heat greater than 40° (104° F.) should be used in the preparation of mustard cataplasms. 

Myron Bender had reported that a meta-f-butylphenyl acetate (4) acetylated 8-cyclodextrin in water with a rate 250 times as fast as that for hydrolysis of that same substrate at the same pH. We had shown that the same reaction was even faster in a mixed DMSO/ water solvent, but still the acceleration was not what one would have hoped for. Model-building suggested that in the acylation reaction the tetrahedral intermediate is partly pulled out of the cavity, so cyclodextrin binding is to some extent fighting against the reaction rate. Thus we made a new substrate, the p-nitrophenyl ester of ferrocene-acrylic acid (5), and saw that it acylated jS-cyclodextrin with a rate acceleration of 51,000 compared with the hydrolysis rate in free solution. With this substrate there... 

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