15985-39-4 Usage
Chemical Properties
White Crystalline Powder
Uses
Different sources of media describe the Uses of 15985-39-4 differently. You can refer to the following data:
1. Methionine sulfoximine inhibits both glutamine synthetase and g-glutamylcysteine synthetase. Working concentrations for inhibition of g-glutamylcysteine synthetase are 0.2-2.0 mM (52% inhibition occured at 100 mM).
Methionine sulfoximine is also a toxic
2. glutamine synthetase inhibitor, ornithine decarboxylase enhancer, convulsant
3. L-Methionine sulfoximine has been used as a potent inhibitor of glutamine synthetase (GS) activity.
Biochem/physiol Actions
As a potent inhibitor of glutamine synthetase activity (GS), this reagent has widely been used as a selection agent for plasmid integration in Chinese hamster ovary (CHO) and other mammalian cell lines. The growing demand for high yield cell banks for production of recombinant proteins for therapeutics has resulted in two major systems for selection of stable and active clones, Methotrexate selection of dihydrofolate reductase (DHFR) overexpressing cells and MSX selection of glutamine synthetase overexpressing cells. Cells are grown in the absence of glutamine in the media and inhibition of the endogenous activity of glutamine synthetase results in cell death for cells lacking overexpression. The MSX-glutamine synthetase selection mechanism provides benefits over that of the Methotrexate-DHFR system in that it typically requires a single amplification step and results in significant reduction of time to produce high stability, highly amplified clones. L-Methionine sulfoximine (MSX) enhances NH3 production in seedling leaves wheat, barley, corn and sorghum plants by inhibiting GS activity. MSX increases ornithine decarboxylase activity and decreases the survival rate in a model of transient cerebral ischemia.
Check Digit Verification of cas no
The CAS Registry Mumber 15985-39-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,9,8 and 5 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 15985-39:
(7*1)+(6*5)+(5*9)+(4*8)+(3*5)+(2*3)+(1*9)=144
144 % 10 = 4
So 15985-39-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H11NO2S.H3NOS/c1-9-3-2-4(6)5(7)8;1-3-2/h4H,2-3,6H2,1H3,(H,7,8);1H,3H2/t4-;/m0./s1
15985-39-4Relevant articles and documents
Straightforward Strategies for the Preparation of NH-Sulfox-imines: A Serendipitous Story
Bull, James A.,Degennaro, Leonardo,Luisi, Renzo
, p. 2525 - 2538 (2017/11/28)
Sulfoximines are emerging as valuable new isosteres for use in medicinal chemistry, with the potential to modulate physicochemical properties. Recent developments in synthetic strategies have made the unprotected 'free' NH-sulfoximine group more readily available, facilitating further study. This account reviews approaches to NH-sulfoximines, with a focus on our contribution to the field. Starting from the development of catalytic strategies involving transition metals, more sustainable metal-free processes have been discovered. In particular, the use of hypervalent iodine reagents to mediate NH-transfer to sulfoxides is described, along with an assessment of the substrate scope. Furthermore, a one-pot strategy to convert sulfides directly into NH-sulfoximines is discussed, with N- and O-transfer occurring under the reaction conditions. Mechanistic evidence for the new procedures is included as well as relevant synthetic applications that further exemplify the potential of these approaches. 1 Introduction 2 Strategies to Form NH-Sulfoximines Involving Transition-Metal Catalysts 3 Metal-Free Strategies to Prepare NH-Sulfoximines 4 Mechanistic Evidence for the Direct Synthesis of NH-Sulfoximines from Sulfoxides and Sulfides 5 Further Applications 6 Conclusion.
QUANTITATIVE SEPARATION AND ANALYSIS OF DIASTEREOMERS OF L-METHIONINE-S,R-SULFOXIMINE VIA CYCLIC N-BLOCKED DERIVATIVES
Sugiyama, Yuichi,Wedler, Frederick C.
, p. 1471 - 1474 (2007/10/02)
The diastereomers of L-methionine-S,R-sulfoximine, blocked at α-N with phthaloyl, then cyclized with Ac2O to form 3,4,5,6-tetrahydro-1-methyl-3-oxo-4-(N-phthalimido)-1,2-thiazine-1-oxide, could be easily separated by fractional crystallization or HPLC, whereas the parent compounds were very difficult to separate.
