A fusion method for the preparation of steroid sulfates

Dusza, John P.; Joseph, Joseph P.; Bernstein, Seymour

doi:10.1016/0039-128x(85)90080-7

Cited by 5 publications

(3 citation statements)

References 4 publications

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“…We hypothesized that the differences in the chemical shifts were due to the presence of a 3β- O -sulfate in 2 . Therefore, cholesterol sulfate ( 6 ) was prepared and its 1 H NMR spectrum (in CD 3 OD) exhibited an excellent match in the multiplicity and chemical shift of protons H2−H7 (Figure ). From this comparison we deduced the identity between the A/B ring substructure of cholesterol sulfate ( 6 ) and PSDS ( 2 ).…”

Section: Resultsmentioning

confidence: 99%

Details of the Structure Determination of the Sulfated Steroids PSDS and PADS: New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone

et al. 2007

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The discovery of two new components of the migratory pheromone used by sea lamprey to guide adults to spawning grounds was recently reported. These hold promise for use in a pheromone-based control program for this species, an invasive pest in the Great Lakes. Details of the structure determination of these steroidal bis-sulfates [petromyzosterol disulfate (PSDS, 2) and petromyzonamine disulfate (PADS, 3)] are described here. Pattern matching of 1H NMR data was particularly valuable. This involved comparison of spectra of the natural samples of 2 and 3 with those of appropriate steroidal analogues [e.g., petromyzonol sulfate (PS, 1, a previously known sea lamprey bile acid derivative that is a third component of the migratory pheromone), cholesterol sulfate (6), and squalamine (8)] and model compounds containing the unprecedented aminolactam substructure present in 3. The logic underlying the iterative analyses used is presented.

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Section: Resultsmentioning

confidence: 99%

Details of the Structure Determination of the Sulfated Steroids PSDS and PADS: New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone

et al. 2007

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“…Hydroxypropyl-β-cyclodextrin (HPBCD) and CoCl 2 were purchased from Sigma-Aldrich (St. Louis, MO). LXR antagonists cholesterol-3-sulfate (ChS) and 7kCh-3-sulfate (7kChS) were synthesized as previously described24 and were purified by HPLC. Their authenticity was verified by LC-MS.…”

Section: Methodsmentioning

confidence: 99%

7-Ketocholesterol Is Present in Lipid Deposits in the Primate Retina: Potential Implication in the Induction of VEGF and CNV Formation

Moreira¹,

Larráyoz²,

Lee³

et al. 2009

Invest. Ophthalmol. Vis. Sci.

147

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PURPOSE 7-Ketocholesterol is a highly toxic oxysterol found in abundance in atherosclerotic plaques and is believed to play a critical role in atherosclerosis. The purpose of this study was to identify and localize 7-ketocholesterol (7kCh) in the primate retina and to examine the potential consequences of its presence in oxidized lipid deposits in the retina. METHODS Unsterified 7kCh was identified and quantified by high-performance liquid chromatography-mass spectrometry. Localization of 7kCh was performed by immunohistochemistry. VEGF induction was determined by qRT-PCR. Cell viability was determined by measuring cellular dehydrogenase activity. Analyses were performed using ARPE19 and human vascular endothelial cells (HMVECs). RESULTS 7-Ketocholesterol is localized mainly to deposits in the choriocapillaris and Bruch’s membrane and on the surfaces of vascular endothelial cells of the neural retina. RPE/choriocapillaris regions contained approximately four times more 7kCh than the neural retina. In ARPE19 cells and HMVECs, oxidized LDL and 7kCh induced VEGF 8- to 10-fold above controls. Hypoxia inducible factor (HIF)-1α levels did not increase as a result of 7kCh treatment, suggesting an HIF-independent induction pathway. Cholesterol sulfate, a liver X receptor (LXR) antagonist, had marked attenuation of the 7kCh-mediated VEGF induction. LXR-specific siRNAs also reduced VEGF induction. Inhibition of NF-κB with BAY 11-7082 reduced IL-8 but not VEGF induction. CONCLUSIONS The location of 7-kCh in the retina and its induction of VEGF in cultured RPE cells and HMVECs suggest it may play a critical role in choroidal neovascularization. The pathway for VEGF induction seems to be independent of HIF-1α and NF-κB but seems to be partially regulated by LXRs.

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“…Sulfurylation (often also termed as sulfation) of biomolecules plays an important role in biological functions such as signal transduction, hormone regulation, molecular recognition, and detoxification (Wong, Chapman, Best, & Hanson, ). Industrial sulfurylation involves sulfuric or sulfamic acid (Al‐Horani & Desai, ), sulfur trioxide‐amine complexes (Dusza, Joseph, & Bernstein, ), and protection‐deprotection strategies (Penney & Perlin, ), which usually lacks regio‐ and chemoselectivity (Simpson & Widlanski, ). Chemical sulfurylation generally require several steps and employ hazardous chemicals (e.g., sulfur trioxide‐pyridine, sulfuric acid, and dicyclohexylcarbodiimide) (Simpson & Widlanski, ).…”

Section: Introductionmentioning

confidence: 99%

A robust protocol for directed aryl sulfotransferase evolution toward the carbohydrate building block GlcNAc

Islam

Maté

Martínez

et al. 2018

Biotech & Bioengineering

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Bacterial aryl sulfotransferases (AST) utilize p-nitrophenylsulfate (pNPS) as a phenolic donor to sulfurylate typically a phenolic acceptor. Interest in aryl sulfotransferases is growing because of their broad variety of acceptors and cost-effective sulfuryl-donors. For instance, aryl sulfotransferase A (ASTA) from Desulfitobacterium hafniense was recently reported to sulfurylate d-glucose. In this study, a directed evolution protocol was developed and validated for aryl sulfotransferase B (ASTB). Thereby the well-known pNPS quantification system was advanced to operate efficiently as a continuous screening system in 96-well MTP format with a true coefficient of variation of 14.3%. A random mutagenesis library (SeSaM library) of ASTB was screened (1,760 clones) to improve sulfurylation of the carbohydrate building block N-acetylglucosamine (GlcNAc). The beneficial variant ASTB-V1 (Val579Asp) showed an up to 3.4-fold increased specific activity toward GlcNAc when compared to ASTB-WT. HPLC- and MS-analysis confirmed ASTB-V1's increased GlcNAc monosulfurylation (2.4-fold increased product formation) representing the validation of the first successful directed evolution round of an AST for a saccharide substrate.

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A fusion method for the preparation of steroid sulfates

Cited by 5 publications

References 4 publications

Details of the Structure Determination of the Sulfated Steroids PSDS and PADS: New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone

Details of the Structure Determination of the Sulfated Steroids PSDS and PADS: New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone

7-Ketocholesterol Is Present in Lipid Deposits in the Primate Retina: Potential Implication in the Induction of VEGF and CNV Formation

A robust protocol for directed aryl sulfotransferase evolution toward the carbohydrate building block GlcNAc

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