Trimetilamina N-oksida: Perbedaan antara revisi
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{{DISPLAYTITLE:Trimetilamina ''N''-oksida}}
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| ImageAlt = Structural formula
| ImageFile1 = Trimethylamine-N-oxide-3D-balls.png
| ImageSize1 =
| ImageAlt1 = Ball-and-stick model
| PIN = ''N'',''N''-dimethylmethanamine oxide
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| Density =
| MeltingPtC = 220 hingga 222
| MeltingPt_notes = (hidrat: 96
| BoilingPt =
| Solubility = baik
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'''Trimetilamina ''N''-oksida''' ('''TMAO''') adalah [[senyawa organik]] dalam golongan [[amina oksida]] dengan [[rumus kimia|rumus]] (CH<sub>3</sub>)<sub>3</sub>NO.
== Sintesis ==
TMAO dapat disintesis dari trimetilamina melalui perlakuan dengan hidrogen peroksida:<ref name=EROS>A. J. Pearson "Trimethylamine N-Oxide" in ''Encyclopedia of Reagents for Organic Synthesis'', John Wiley & Sons, 2001: New York. {{DOI|10.1002/047084289X.rt268}}</ref>
:H<sub>2</sub>O<sub>2</sub> + (CH<sub>3</sub>)<sub>3</sub>N → H<sub>2</sub>O + (CH<sub>3</sub>)<sub>3</sub>NO
TMAO dibiosintesikan dari [[trimetilamina]], yang berasal dari [[kolin]].<ref>{{Cite journal |author1=Baker, J.R. |author2=Chaykin, S. | title = The biosynthesis of trimethylamine-''N''-oxide | journal = [[J. Biol. Chem.]] | date=1 April 1962| volume = 237 | pages = 1309–13 |url = http://www.jbc.org/cgi/content/citation/237/4/1309 | pmid = 13864146 | issue = 4 }}</ref>
== Trimethilaminuria ==
[[Trimethilaminuria]] adalah cacat langka dalam produksi enzim [[flavin mengandung monooksigenase 3]] (''FMO3'').<ref>{{cite journal | author=Treacy, E.P.| title=Mutations of the flavin-containing monooxygenase gene (''FMO3'') cause trimethylaminuria, a defect in detoxication | journal=Human Molecular Genetics | year=1998 | pages=839–45 | volume=7 | issue=5| doi=10.1093/hmg/7.5.839 | pmid=9536088 | display-authors=2 | last2=Akerman | first2=BR | last3=Chow | first3=LM | last4=Youil | first4=R | last5=Bibeau | first5=C | last6=Lin | first6=J | last7=Bruce | first7=AG | last8=Knight | first8=M | last9=Danks | first9=DM}}</ref><ref>{{cite journal |vauthors=Zschocke J, Kohlmueller D, Quak E, Meissner T, Hoffmann GF, Mayatepek E | title=Mild trimethylaminuria caused by common variants in FMO3 gene | journal=Lancet | year=1999 | pages=834–5 | volume=354 | issue=9181 | pmid=10485731 | doi=10.1016/S0140-6736(99)80019-1}}</ref> Mereka yang mengalami trimethilaminuria tidak dapat mengubah trimetilamina turunan [[kolin]] menjadi trimetilamina oksida. Trimethilamina kemudian terakumulasi dan dilepaskan dalam keringat, urin, dan napas seseorang, mengeluarkan bau amis kuat.
== Aplikasi laboratorium ==
Trimethilamina oksida digunakan dalam percobaan [[perlipatan protein]] untuk menetralkan efek yang berkembang dari [[urea]].<ref>{{cite journal | author=Zou, Q. | title=The Molecular Mechanism of Stabilization of Proteins by TMAO and Its Ability to Counteract the Effects of Urea| journal=[[J. Am. Chem. Soc.]] | year=2002 | volume=124 | issue=7 | pages= 1192–1202 | doi=10.1021/ja004206b | pmid=11841287 | display-authors=1 | last2=Bennion | first2=Brian J. | last3=Daggett | first3=Valerie | last4=Murphy | first4=Kenneth P.}}</ref>
Dalam reaksi [[kimia organometalik]] dari [[abstraksi nukleofilik]], Me<sub>3</sub>NO digunakan sebagai agen dekarbonilasi menurut stoikiometri berikut ini:
:M(CO)<sub>n</sub> + Me<sub>3</sub>NO + L → M(CO)<sub>n-1</sub>L + Me<sub>3</sub>N + CO<sub>2</sub>
Reaksi ini digunakan untuk dekompleks ligan organik dari logam, seperti dari (diena)Fe(CO)<sub>3</sub>.<ref name=EROS/>
Hal ini digunakan dalam reaksi oksidasi tertentu, seperti konversi alkil iodida menjadi [[aldehida]] yang sesuai.<ref>{{OrgSynth | author = Volker Franzen | title = Octanal | collvol = 5 | collvolpages = 872 | prep = cv5p0872 | year = 1973}}</ref>
== Hubungan mikrobiotik ==
Ordo ''[[Clostridiales]]'', genus ''[[Ruminococcus]]'', dan takson ''Lachnospiraceae'' berhubungan positif dengan tingkat TMA dan TMAO.<ref name=cell.2015.11.055/> Sebaliknya, proporsi S24-7, famili yang melimpah dari ''[[Bacteroidetes]]'', berbanding terbalik dengan tingkat TMA dan TMAO.<ref name=cell.2015.11.055>{{cite journal|last1=Wang|first1=Zeneng|last2=Roberts|first2=Adam B.|last3=Buffa|first3=Jennifer A.|last4=Levison|first4=Bruce S.|last5=Zhu|first5=Weifei|last6=Org|first6=Elin|last7=Gu|first7=Xiaodong|last8=Huang|first8=Ying|last9=Zamanian-Daryoush|first9=Maryam|last10=Culley|first10=Miranda K.|last11=DiDonato|first11=Anthony J.|last12=Fu|first12=Xiaoming|last13=Hazen|first13=Jennie E.|last14=Krajcik|first14=Daniel|last15=DiDonato|first15=Joseph A.|last16=Lusis|first16=Aldons J.|last17=Hazen|first17=Stanley L.|title=Non-lethal Inhibition of Gut Microbial Trimethylamine Production for the Treatment of Atherosclerosis|journal=Cell|date=December 2015|volume=163|issue=7|pages=1585–1595|doi=10.1016/j.cell.2015.11.055|url=http://www.cell.com/cell/fulltext/S0092-8674(15)01574-3 | quote=<br/>• A structural analog of choline, 3,3-dimethyl-1-butanol (DMB), is shown to non-lethally inhibit TMA formation from cultured microbes, to inhibit distinct microbial TMA lyases, and to both inhibit TMA production from physiologic polymicrobial cultures (e.g., intestinal contents, human feces) and reduce TMAO levels in mice fed a high-choline or L-carnitine diet.<br/>• DMB was detected in some balsamic vinegars, in red wines, and in some cold-pressed extra virgin olive oils and grape seed oils|pmid=26687352|pmc=4871610}}</ref>
== Referensi ==
{{reflist}}
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