Trimetilamina N-oksida

Trimethylamine N-oxide
Nama


Nama IUPAC trimethylamine oxide
Nama IUPAC (preferensi) N,N-dimethylmethanamine oxide
Nama lain trimethylamine oxide, TMAO, TMANO
Penanda
Nomor CAS	1184-78-7^Y
Model 3D (JSmol)	Gambar interaktif
ChEBI	CHEBI:15724^Y
ChemSpider	1113^Y
Nomor EC
KEGG	C01104^Y
PubChem CID	1145
Nomor RTECS	{{{value}}}
UNII	FLD0K1SJ1A^Y
CompTox Dashboard (EPA)	DTXSID001030179 DTXSID8049678, DTXSID001030179
InChI InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3^Y Key: UYPYRKYUKCHHIB-UHFFFAOYSA-N^Y InChI=1/C3H9NO/c1-4(2,3)5/h1-3H3 Key: UYPYRKYUKCHHIB-UHFFFAOYAU
SMILES C[N+](C)(C)[O-]
Sifat
Rumus kimia	C₃H₉NO
Massa molar	75,11
Penampilan	padatan tak berwarna
Titik lebur	220 hingga^{[convert: unit tak dikenal]} (hidrat: 96 °C)
Kelarutan dalam air	baik
Kecuali dinyatakan lain, data di atas berlaku pada suhu dan tekanan standar (25 °C [77 °F], 100 kPa).
Y verifikasi (apa ini ^YN ?)
Referensi

Chemical compoundTemplat:SHORTDESC:Chemical compound

Trimetilamina N-oksida (TMAO) adalah senyawa organik dalam golongan amina oksida dengan rumus (CH₃)₃NO. Padatan tak berwarna ini biasanya dijumpai sebagai dihidrat. Ini adalah produk oksidasi trimetilamina, metabolit yang umum pada hewan. Trimetilamina N-oksida' merupakan suatu osmolit yang ditemukan pada ikan air asin, hiu, pari, moluska, dan krustasea. Ia merupakan penstabil protein yang dapat berfungsi untuk menetralkan urea, osmolit utama hiu, skate, dan pari. Kandungannya juga lebih tinggi pada ikan laut dalam dan krustasea, di mana ia dapat melawan efek tekanan destabilisasi protein.^[1] TMAO terurai menjadi trimetilamina (TMA), yang merupakan odoran utama yang menjadi karateristik makanan laut yang membusuk.

Sintesis

TMAO dapat disintesis dari trimetilamina melalui perlakuan dengan hidrogen peroksida:^[2]

H₂O₂ + (CH₃)₃N → H₂O + (CH₃)₃NO

TMAO dibiosintesikan dari trimetilamina, yang berasal dari kolin.^[3]

Trimethilaminuria

Trimethilaminuria adalah cacat langka dalam produksi enzim flavin mengandung monooksigenase 3 (FMO3).^[4]^[5] 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.^[6]

Dalam reaksi kimia organometalik dari abstraksi nukleofilik, Me₃NO digunakan sebagai agen dekarbonilasi menurut stoikiometri berikut ini:

M(CO)_n + Me₃NO + L → M(CO)_n-1L + Me₃N + CO₂

Reaksi ini digunakan untuk dekompleks ligan organik dari logam, seperti dari (diena)Fe(CO)₃.^[2]

Hal ini digunakan dalam reaksi oksidasi tertentu, seperti konversi alkil iodida menjadi aldehida yang sesuai.^[7]

Hubungan mikrobiotik

Ordo Clostridiales, genus Ruminococcus, dan takson Lachnospiraceae berhubungan positif dengan tingkat TMA dan TMAO.^[8] Sebaliknya, proporsi S24-7, famili yang melimpah dari Bacteroidetes, berbanding terbalik dengan tingkat TMA dan TMAO.^[8]

Referensi

↑ Yancey, P. (2005). "Organic osmolytes as compatible, metabolic, and counteracting cytoprotectants in high osmolarity and other stresses". J. Exp. Biol. 208 (15): 2819–2830. doi:10.1242/jeb.01730. PMID 16043587.
1 2 A. J. Pearson "Trimethylamine N-Oxide" in Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, 2001: New York. doi:10.1002/047084289X.rt268
↑ Baker, J.R.; Chaykin, S. (1 April 1962). "The biosynthesis of trimethylamine-N-oxide". J. Biol. Chem. 237 (4): 1309–13. PMID 13864146.
↑ Treacy, E.P.; Akerman, BR; et al. (1998). "Mutations of the flavin-containing monooxygenase gene (FMO3) cause trimethylaminuria, a defect in detoxication". Human Molecular Genetics. 7 (5): 839–45. doi:10.1093/hmg/7.5.839. PMID 9536088.
↑ Zschocke J, Kohlmueller D, Quak E, Meissner T, Hoffmann GF, Mayatepek E (1999). "Mild trimethylaminuria caused by common variants in FMO3 gene". Lancet. 354 (9181): 834–5. doi:10.1016/S0140-6736(99)80019-1. PMID 10485731.
↑ Zou, Q.; et al. (2002). "The Molecular Mechanism of Stabilization of Proteins by TMAO and Its Ability to Counteract the Effects of Urea". J. Am. Chem. Soc. 124 (7): 1192–1202. doi:10.1021/ja004206b. PMID 11841287.
↑ Volker Franzen (1973). "Octanal". Org. Synth.; Coll. Vol. 5: 872.
1 2 • 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":{"wt":"26687352"},"pmc":{"wt":"4871610"}},"i":0}}]}' id="mw2w"/>Wang, Zeneng; Roberts, Adam B.; Buffa, Jennifer A.; Levison, Bruce S.; Zhu, Weifei; Org, Elin; Gu, Xiaodong; Huang, Ying; Zamanian-Daryoush, Maryam; Culley, Miranda K.; DiDonato, Anthony J.; Fu, Xiaoming; Hazen, Jennie E.; Krajcik, Daniel; DiDonato, Joseph A.; Lusis, Aldons J.; Hazen, Stanley L. (December 2015). "Non-lethal Inhibition of Gut Microbial Trimethylamine Production for the Treatment of Atherosclerosis". Cell. 163 (7): 1585–1595. doi:10.1016/j.cell.2015.11.055. PMC 4871610. PMID 26687352.
• 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.
• DMB was detected in some balsamic vinegars, in red wines, and in some cold-pressed extra virgin olive oils and grape seed oils

[1] Yancey, P. (2005). "Organic osmolytes as compatible, metabolic, and counteracting cytoprotectants in high osmolarity and other stresses". J. Exp. Biol. 208 (15): 2819–2830. doi:10.1242/jeb.01730. PMID 16043587.

[EROS-2] 1 2 A. J. Pearson "Trimethylamine N-Oxide" in Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, 2001: New York. doi:10.1002/047084289X.rt268

[3] Baker, J.R.; Chaykin, S. (1 April 1962). "The biosynthesis of trimethylamine-N-oxide". J. Biol. Chem. 237 (4): 1309–13. PMID 13864146.

[4] Treacy, E.P.; Akerman, BR; et al. (1998). "Mutations of the flavin-containing monooxygenase gene (FMO3) cause trimethylaminuria, a defect in detoxication". Human Molecular Genetics. 7 (5): 839–45. doi:10.1093/hmg/7.5.839. PMID 9536088.

[5] Zschocke J, Kohlmueller D, Quak E, Meissner T, Hoffmann GF, Mayatepek E (1999). "Mild trimethylaminuria caused by common variants in FMO3 gene". Lancet. 354 (9181): 834–5. doi:10.1016/S0140-6736(99)80019-1. PMID 10485731.

[6] Zou, Q.; et al. (2002). "The Molecular Mechanism of Stabilization of Proteins by TMAO and Its Ability to Counteract the Effects of Urea". J. Am. Chem. Soc. 124 (7): 1192–1202. doi:10.1021/ja004206b. PMID 11841287.

[7] Volker Franzen (1973). "Octanal". Org. Synth.; Coll. Vol. 5: 872.

[cell.2015.11.055-8] 1 2 • 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":{"wt":"26687352"},"pmc":{"wt":"4871610"}},"i":0}}]}' id="mw2w"/>Wang, Zeneng; Roberts, Adam B.; Buffa, Jennifer A.; Levison, Bruce S.; Zhu, Weifei; Org, Elin; Gu, Xiaodong; Huang, Ying; Zamanian-Daryoush, Maryam; Culley, Miranda K.; DiDonato, Anthony J.; Fu, Xiaoming; Hazen, Jennie E.; Krajcik, Daniel; DiDonato, Joseph A.; Lusis, Aldons J.; Hazen, Stanley L. (December 2015). "Non-lethal Inhibition of Gut Microbial Trimethylamine Production for the Treatment of Atherosclerosis". Cell. 163 (7): 1585–1595. doi:10.1016/j.cell.2015.11.055. PMC 4871610. PMID 26687352.
• 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.
• DMB was detected in some balsamic vinegars, in red wines, and in some cold-pressed extra virgin olive oils and grape seed oils

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[2]

[3]

[4]

[5]

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[7]

[8]

Sintesis

Trimethilaminuria

Aplikasi laboratorium

Hubungan mikrobiotik

Referensi

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