About: Synthesis of deuterium labeled NMDA receptor inhibitor-20-Oxo-5 beta-[9,12,12-H-2(3)]pregnan-3 alpha-yl-L-glutamyl 1-ester

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About: Synthesis of deuterium labeled NMDA receptor inhibitor-20-Oxo-5 beta-[9,12,12-H-2(3)]pregnan-3 alpha-yl-L-glutamyl 1-ester Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://www.sciencedirect.com/science/article/pii/S0039128X11003898
Description	20-Oxo-5 beta-[9,12,12-H-2(3)]pregnan-3 alpha-yl-L-glutamyl 1-ester 11 was synthesized as an internal standard for quantification of a neuroprotective NMDA receptor ligand, 20-oxo-5 beta-pregnan-3 alpha-yl-L-glutamyl 1-ester 18 and its metabolites, in plasma and tissue. 11 alpha-Hydroxy-progesterone (1) was reduced under basic conditions to yield the corresponding 5 beta-steroid. Protection of the 3- and 20-oxo groups and oxidation of the 11 alpha-hydroxy group was then followed by a deuterium exchange, conducted under basic conditions using deuterated methanol. Next, the carbonyl moiety at C-11 was reduced and the 11 alpha-hydroxyl group removed through utilization of the Barton-McCombie reaction. Subsequent deprotection of the 3- and 20-acetals and stereoselective reduction of the 3-oxo group gave the desired trideuterated pregnanolone (8). This was coupled with protected glutamic acid, which was then deprotected to yield [9,12,12-H-2(3)]-pregnanolone glutamate (11) with }99% isotopic purity 20-Oxo-5 beta-[9,12,12-H-2(3)]pregnan-3 alpha-yl-L-glutamyl 1-ester 11 was synthesized as an internal standard for quantification of a neuroprotective NMDA receptor ligand, 20-oxo-5 beta-pregnan-3 alpha-yl-L-glutamyl 1-ester 18 and its metabolites, in plasma and tissue. 11 alpha-Hydroxy-progesterone (1) was reduced under basic conditions to yield the corresponding 5 beta-steroid. Protection of the 3- and 20-oxo groups and oxidation of the 11 alpha-hydroxy group was then followed by a deuterium exchange, conducted under basic conditions using deuterated methanol. Next, the carbonyl moiety at C-11 was reduced and the 11 alpha-hydroxyl group removed through utilization of the Barton-McCombie reaction. Subsequent deprotection of the 3- and 20-acetals and stereoselective reduction of the 3-oxo group gave the desired trideuterated pregnanolone (8). This was coupled with protected glutamic acid, which was then deprotected to yield [9,12,12-H-2(3)]-pregnanolone glutamate (11) with }99% isotopic purity (en)
Title	Synthesis of deuterium labeled NMDA receptor inhibitor-20-Oxo-5 beta-[9,12,12-H-2(3)]pregnan-3 alpha-yl-L-glutamyl 1-ester Synthesis of deuterium labeled NMDA receptor inhibitor-20-Oxo-5 beta-[9,12,12-H-2(3)]pregnan-3 alpha-yl-L-glutamyl 1-ester (en)
skos:prefLabel	Synthesis of deuterium labeled NMDA receptor inhibitor-20-Oxo-5 beta-[9,12,12-H-2(3)]pregnan-3 alpha-yl-L-glutamyl 1-ester Synthesis of deuterium labeled NMDA receptor inhibitor-20-Oxo-5 beta-[9,12,12-H-2(3)]pregnan-3 alpha-yl-L-glutamyl 1-ester (en)
skos:notation	RIV/61989592:15310/12:33143005!RIV13-MSM-15310___
http://linked.open...avai/riv/aktivita	I P Z
http://linked.open...avai/riv/aktivity	I, P(1M0517), P(ED0007/01/01), P(IAA400550801), P(LC06077), P(LC554), P(NS10365), Z(AV0Z40550506), Z(AV0Z50110509), Z(MSM6198959216)
http://linked.open...iv/cisloPeriodika	3
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Chodounská, Hana
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Palackého v Olomouci / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	172957
http://linked.open...ai/riv/idVysledku	RIV/61989592:15310/12:33143005
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Deuterium labeling; Neuroprotection; NMDA receptor (en)
http://linked.open.../riv/klicoveSlovo	NMDA receptor Deuterium labeling Neuroprotection
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[FBDCBD88225F]
http://linked.open...i/riv/nazevZdroje	Steroids
http://linked.open...in/vavai/riv/obor	CE
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	6 (xsd:int)
http://linked.open...vavai/riv/projekt	Synthesis of tritium labelled brassinosteroids and their application in the studies of their mechanism of action on molecular level. Center of Neuropsychiatric Studies 2005-2009 (Neurobiology in Clinical Application) Neuroscience Centre Centre of the Region Haná for Biotechnological and Agricultural Research Center of Chemical Genetics Biological activity and pharmacokinetic properties of 3?C substituted derivatives of pregnanolone
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	77
http://linked.open...iv/tvurceVysledku	Chodounská, Hana Kapras, Vojtěch Valeš, Karel Šťastná, Eva Vyklický, Ladislav Slavíčková, Alena
http://linked.open...ain/vavai/riv/wos	000300523000015
http://linked.open...n/vavai/riv/zamer	Regulace biologických procesů: Chemické modulátory vybraných systémů významných pro medicínu a zemědělství Výzkum molekulárních a buněčných základů fyziologických a patofyziologických procesů s cílem objasnit mechanismy vzniku závažných onemocnění člověka Modulation of signalling and regulatory pathways in normal and cancer cells
issn	0039-128X
number of pages	6 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.steroids.2011.12.019
http://localhost/t...ganizacniJednotka	15310

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