Boc-D-Methioninol
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Boc-D-Methioninol

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category
Amino Alcohol
Catalog number
BAT-002593
CAS number
91177-57-0
Molecular Formula
C10H21NO3S
Molecular Weight
235.3
Boc-D-Methioninol
IUPAC Name
tert-butyl N-[(2R)-1-hydroxy-4-methylsulfanylbutan-2-yl]carbamate
Synonyms
Boc-D-Met-ol; (R)-tert-Butyl (1-hydroxy-4-(methylthio)butan-2-yl)carbamate; tert-Butyl (R)-1-hydroxy-4-(methylthio)butan-2-ylcarbamate
Appearance
White powder
Purity
≥ 98% (HPLC)
Melting Point
47-53 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C10H21NO3S/c1-10(2,3)14-9(13)11-8(7-12)5-6-15-4/h8,12H,5-7H2,1-4H3,(H,11,13)/t8-/m1/s1
InChI Key
IPIBDQMAIDPJBU-MRVPVSSYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCSC)CO
1.Design, synthesis and evaluation of a cellular stable and detectable biotinylated fumagillin probe and investigation of cell permeability of fumagillin and its analogs to endothelial and cancer cells.
Zhou GC1, Liu F, Wan J, Wang J, Wang D, Wei P, Ouyang P. Eur J Med Chem. 2013;70:631-9. doi: 10.1016/j.ejmech.2013.10.033. Epub 2013 Oct 25.
Fumagillin (1), a natural product of fungal origin, and its analogs were discovered to be extremely potent and highly selective inhibitors restraining endothelial cell proliferation in vitro by covalently binding to MetAP2. In order to further understand the unclear biological mechanisms and pharmacological processes of fumagillin and its derivatives, fumagillin-biotin conjugate 8 was designed and synthesized, which is linked with a 27-atom connection chain and by urethane (carbamate) bonds between fumagillol and D-norbiotinamine. The conjugate 8 shows comparable activity and selectivity against HUVEC proliferation as fumagillin. It was demonstrated that the conjugate 8 is stable inside the cell and its linker is of a suitable length for the detection of biotin in native and denatured conditions. Using the conjugate 8, it was determined that the cell permeability of fumagillin (1) and its analogs are not responsible for their inhibitory activity difference against the proliferation of endothelial and cancer cells.
2.Cathepsin G-regulated release of formyl peptide receptor agonists modulate neutrophil effector functions.
Woloszynek JC1, Hu Y, Pham CT. J Biol Chem. 2012 Oct 5;287(41):34101-9. doi: 10.1074/jbc.M112.394452. Epub 2012 Aug 9.
Neutrophil serine proteases play an important role in inflammation by modulating neutrophil effector functions. We have previously shown that neutrophils deficient in the serine proteases cathepsin G and neutrophil elastase (CG/NE neutrophils) exhibit severe defects in chemokine CXCL2 release and reactive oxygen species (ROS) production when activated on immobilized immune complex. Exogenously added active CG rescues these defects, but the mechanism remains undefined. Using a protease-based proteomic approach, we found that, in vitro, the addition of exogenous CG to immune complex-stimulated CG/NE neutrophils led to a decrease in the level of cell-associated annexin A1 (AnxA1) and cathelin-related antimicrobial peptide (CRAMP), both known inflammatory mediators. We further confirmed that, in vivo, CG was required for the extracellular release of AnxA1 and CRAMP in a subcutaneous air pouch model. In vitro, CG efficiently cleaved AnxA1, releasing the active N-terminal peptide Ac2-26, and processed CRAMP in limited fashion.
3.The development of a new class of inhibitors for betaine-homocysteine S-methyltransferase.
Pícha J1, Vaněk V, Buděšínský M, Mládková J, Garrow TA, Jiráček J. Eur J Med Chem. 2013 Jul;65:256-75. doi: 10.1016/j.ejmech.2013.04.039. Epub 2013 Apr 30.
Betaine-homocysteine S-methyltransferase (BHMT) is an important zinc-dependent methyltransferase that uses betaine as the methyl donor for the remethylation of homocysteine to form methionine. In the liver, BHMT performs to half of the homocysteine remethylation. In this study, we systematically investigated the tolerance of the enzyme for modifications at the "homocysteine" part of the previously reported potent inhibitor (R,S)-5-(3-amino-3-carboxy-propylsulfanyl)-pentanoic acid (1). In the new compounds, which are S-alkylated homocysteine derivatives, we replaced the carboxylic group in the "homocysteine" part of inhibitor 1 with different isosteric moieties (tetrazole and oxadiazolone); we suppressed the carboxylic negative charge by amidations; we enhanced acidity by replacing the carboxylate with phosphonic or phosphinic acids; and we introduced pyrrolidine steric constraints. Some of these compounds display high affinity toward human BHMT and may be useful for further pharmacological studies of this enzyme.
4.Synthesis of Sulfoximine Carbamates by Rhodium-Catalyzed Nitrene Transfer of Carbamates to Sulfoxides.
Zenzola M1,2, Doran R1, Luisi R2, Bull JA1. J Org Chem. 2015 Jun 19;80(12):6391-9. doi: 10.1021/acs.joc.5b00844. Epub 2015 Jun 2.
Sulfoximines are of considerable interest for incorporation into medicinal compounds. A convenient synthesis of N-protected sulfoximines is achieved, under mild conditions, by rhodium-catalyzed transfer of carbamates to sulfoxides. The first examples of 4-membered thietane-oximines are prepared. Sulfoximines bearing Boc and Cbz groups are stable to further cross coupling reactions, and readily deprotected. This method may facilitate the preparation of NH-sulfoximines providing improved (global) deprotection strategies, which is illustrated in the synthesis of methionine sulfoxide (MSO).
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