Synthesa a charakterisace aduktů styrenoxidu s cysteinem, histidinem a lysinem v lidském globinu.

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F07%3A00018504" target="_blank" >RIV/60461373:22310/07:00018504 - isvavai.cz</a>

Výsledek na webu

—

DOI - Digital Object Identifier

—

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and Characterization of Styrene Oxide Adducts with Cysteine, Histidine, and Lysine in Human Globin

Popis výsledku v původním jazyce

Synthesis of styrene 7,8-oxide (SO) adducts with cysteine, lysine and histidine is described. S-(2-hydroxy-1-phenylethyl)cysteine and S-(2-hydroxy-2-phenylethyl)cysteine were prepared by direct alkylation of cysteine with (R)-SO or (S)-SO enantiomers andisolated by semi-preparative HPLC. To obtain SO adducts with lysine and histidine, N?-Boc protected lysine and histidine derivatives were alkylated with pure SO enantiomers. Deprotection of the Boc group afforded corresponding derivatives. Pure N?-(2-hydroxy-1-phenylethyl)lysine, N?-(2-hydroxy-2-phenylethyl)lysine, or N?-(2-hydroxy-1-phenylethyl)histidine, N?-(2-hydroxy-2-phenylethyl)histidine, N?-(2-hydroxy-1-phenylethyl)histidine, and N?-(2-hydroxy-2-phenylethyl)histidine isomers were isolated by semipreparative HPLC. Structural assignments of these isomers were based on the NMR techniques. The isomers were used to assign the SO adducts in globin incubated with SO in vitro. Deuterated analogues of the SO adducts

Název v anglickém jazyce

Synthesis and Characterization of Styrene Oxide Adducts with Cysteine, Histidine, and Lysine in Human Globin

Popis výsledku anglicky

Synthesis of styrene 7,8-oxide (SO) adducts with cysteine, lysine and histidine is described. S-(2-hydroxy-1-phenylethyl)cysteine and S-(2-hydroxy-2-phenylethyl)cysteine were prepared by direct alkylation of cysteine with (R)-SO or (S)-SO enantiomers andisolated by semi-preparative HPLC. To obtain SO adducts with lysine and histidine, N?-Boc protected lysine and histidine derivatives were alkylated with pure SO enantiomers. Deprotection of the Boc group afforded corresponding derivatives. Pure N?-(2-hydroxy-1-phenylethyl)lysine, N?-(2-hydroxy-2-phenylethyl)lysine, or N?-(2-hydroxy-1-phenylethyl)histidine, N?-(2-hydroxy-2-phenylethyl)histidine, N?-(2-hydroxy-1-phenylethyl)histidine, and N?-(2-hydroxy-2-phenylethyl)histidine isomers were isolated by semipreparative HPLC. Structural assignments of these isomers were based on the NMR techniques. The isomers were used to assign the SO adducts in globin incubated with SO in vitro. Deuterated analogues of the SO adducts

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

—

Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2007

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Chem. Res. Toxicol.

ISSN

0893-228X

e-ISSN

—

Svazek periodika

20

Číslo periodika v rámci svazku

10

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

11

Strana od-do

1442-1452

Kód UT WoS článku

—

EID výsledku v databázi Scopus

—