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Statements

Subject Item
n2:RIV%2F61989592%3A15310%2F12%3A33143005%21RIV13-MSM-15310___
rdf:type
n19:Vysledek skos:Concept
rdfs:seeAlso
http://www.sciencedirect.com/science/article/pii/S0039128X11003898
dcterms: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
dcterms: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
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
skos:notation
RIV/61989592:15310/12:33143005!RIV13-MSM-15310___
n19:predkladatel
n21:orjk%3A15310
n3:aktivita
n5:P n5:I n5:Z
n3:aktivity
I, P(1M0517), P(ED0007/01/01), P(IAA400550801), P(LC06077), P(LC554), P(NS10365), Z(AV0Z40550506), Z(AV0Z50110509), Z(MSM6198959216)
n3:cisloPeriodika
3
n3:dodaniDat
n8:2013
n3:domaciTvurceVysledku
n14:2024438
n3:druhVysledku
n7:J
n3:duvernostUdaju
n11:S
n3:entitaPredkladatele
n20:predkladatel
n3:idSjednocenehoVysledku
172957
n3:idVysledku
RIV/61989592:15310/12:33143005
n3:jazykVysledku
n22:eng
n3:klicovaSlova
Deuterium labeling; Neuroprotection; NMDA receptor
n3:klicoveSlovo
n12:Deuterium%20labeling n12:NMDA%20receptor n12:Neuroprotection
n3:kodStatuVydavatele
US - Spojené státy americké
n3:kontrolniKodProRIV
[FBDCBD88225F]
n3:nazevZdroje
Steroids
n3:obor
n13:CE
n3:pocetDomacichTvurcuVysledku
1
n3:pocetTvurcuVysledku
6
n3:projekt
n6:1M0517 n6:LC06077 n6:ED0007%2F01%2F01 n6:LC554 n6:IAA400550801 n6:NS10365
n3:rokUplatneniVysledku
n8:2012
n3:svazekPeriodika
77
n3:tvurceVysledku
Kapras, Vojtěch Valeš, Karel Chodounská, Hana Vyklický, Ladislav Šťastná, Eva Slavíčková, Alena
n3:wos
000300523000015
n3:zamer
n4:AV0Z40550506 n4:AV0Z50110509 n4:MSM6198959216
s:issn
0039-128X
s:numberOfPages
6
n9:doi
10.1016/j.steroids.2011.12.019
n18:organizacniJednotka
15310