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{{Use dmy dates|date=May 2020}} |
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{{Chembox |
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| verifiedrevid = 412196409 |
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| verifiedrevid = 447003644 |
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|ImageFile=Queuine.svg |
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| ImageFile=Queuine.svg |
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|ImageSize=240px |
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| ImageSize=240px |
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| PIN=2-Amino-5-({amino}methyl)-3,7-dihydro-4''H''-pyrrolopyrimidin-4-one |
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|IUPACName= |
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|OtherNames= 7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanine |
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| OtherNames= 7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanine |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=72496-59-4 |
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| CASNo=72496-59-4 |
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| PubChem=114881 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES=C1=CC(C(C1NCC2=CNC3=C2C(=O)N=C(N3)N)O)O |
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| UNII = DAK6EYX2BZ |
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| MeSHName=Queuine |
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| PubChem=114881 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 102837 |
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| SMILES = C1=C((1NCC2=CNC3=C2C(=O)NC(=N3)N)O)O |
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| InChI = 1/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9+/m0/s1 |
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| InChIKey = WYROLENTHWJFLR-ACLDMZEEBO |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9+/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = WYROLENTHWJFLR-ACLDMZEESA-N |
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| MeSHName=Queuine |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=12 | H=15 | N=5 | O=3 |
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| Formula=C<sub>12</sub>H<sub>15</sub>N<sub>5</sub>O<sub>3</sub> |
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| Appearance= |
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| MolarMass=277,28 g/mol |
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'''Queuine''' ('''Q''') is a ] base found in the first (or ]) position of the ] of ]s specific for Asn, Asp, His, and Tyr, in most ] and ]. |
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'''Queuine''' ({{IPAc-en|k|j|uː|iː|n|}}) ('''Q''') is a hypermodified ] found in the first (or ]) position of the ] of ]s specific for Asn, Asp, His, and Tyr, in most ] and ].<ref>{{cite journal | doi = 10.1080/07328318308078845| title = Queuine, the Q-Containing tRNAs and the Enzymes Responsible for Their Formation| journal = Nucleosides and Nucleotides| volume = 2| pages = 1–20| year = 1983| last1 = Farkas| first1 = Walter R.}}</ref> Because it is utilized by all eukaryotes but produced exclusively by bacteria, it is a putative vitamin.<ref>{{cite book |last1=Bjork |first1=Glenn |last2=Rasmusen |first2=Torgny |title=Modification and Editing of RNA |date=1998 |publisher=ASM Press |location=New York |page=480 |doi=10.1128/9781555818296.ch26 |url=https://onlinelibrary.wiley.com/doi/10.1128/9781555818296.ch26 |quote=Whereas bacteria can synthesize the precursor preQ0, eukaryotic organisms are unable to make queuine and have to rely on the presence of the base in the diet. Queuine can therefore be considered a vitamin.}}</ref> |
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The ] of queuine is ]. Queuine is not found in the tRNA of archaea; however, a related 7-deazaguanine derivative, the nucleoside of which is archaeosine, occurs in different tRNA position, the dihydrouridine loop, and in tRNAs with more specificities. |
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The ] of queuine is ]. Queuine is not found in the tRNA of archaea; however, a related 7-deazaguanine derivative, the nucleoside of which is ], occurs in different tRNA position, the dihydrouridine loop, and in tRNAs with more specificities. |
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== Literature == |
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* Walter R. Farkas: „Queuine, The Q-Containing tRNAs and the Enzymes Responsible for Their Formation“, '']'', '''1983''', ''2'' (1), pp. 1–20; {{DOI|10.1080/07328318308078845}}. |
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* Hiroshi Akimoto, Eiko Imamiya, Takenori Hitaka, Hiroaki Nomura, Susumu Nishimura: „Synthesis of queuine, the base of naturally occurring hypermodified nucleoside (queuosine), and its analogues“, '']'', '''1988''', pp. 1637–1644; {{DOI|10.1039/P19880001637}}. |
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* Florian Klepper: , Dissertation, München 2007. |
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* Florian Klepper, Eva-Maria Jahn, Volker Hickmann, ]: „Synthese des tRNA-Nucleosids Queuosin unter Verwendung eines chiralen Allylazid-Intermediats“, '']'', '''2007''', ''119'' (13), pp. 2377–2379; {{DOI|10.1002/ange.200604579}}. |
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* Florian Klepper, Eva-Maria Jahn, Volker Hickmann, ]: „Synthesis of the Transfer-RNA Nucleoside Queuosine by Using a Chiral Allyl Azide Intermediate“, '']'', '''2007''', ''46'' (13), pp. 2325–2327; {{DOI|10.1002/anie.200604579}}. |
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* Allen F. Brooks, George A. Garcia, H. D. Hollis Showalter: „A short, concise synthesis of queuine“, '']'', '''2010''', ''51'', pp. 4163–4165; {{DOI|10.1016/j.tetlet.2010.06.008}}; . |
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==History and naming== |
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== External Links == |
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In 1967, it was discovered that the four above-mentioned tRNAs contained an as-yet unknown nucleoside, which was designated "Nucleoside Q". This name remained in use throughout much of the work to characterize the compound, after which it was proposed that its common name should be based on the sound of the letter Q—thus producing "queuine" by analogy to ] and other nucleobases, and "queuosine" by analogy to ] and other nucleosides.<ref>{{cite book |
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* Human Metabolome Database: |
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|last1=Nishimura |
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|first1=Susumu |
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|last2=Abraham |
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|first2=Abraham |
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|last3=Brimacombe |
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|first3=Richard |
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|last4=Elliott |
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|first4=Steven |
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|last5=McLaughlin |
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|first5=Calvin |
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|last6=Maly |
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|first6=Peter |
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|last7=Roberts |
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|first7=Edda |
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|last8=Shaw |
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|first8=Joni |
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|last9=Singhal |
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|first9=Ram |
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|last10=Subramanian |
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|first10=Alap-Raman |
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|last11=Vakharia |
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|first11=Vikram |
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|last12=Zwieb |
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|first12=Christian |
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|display-authors=1 |
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|editor1-last=Cohn |
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|editor1-first=Waldo |
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|date=1983 |
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|title=Progress in Nucleic Acid Research and Molecular Biology |
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|volume=28 |
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|url=https://books.google.com/books?id=0IM73gjuKqoC |
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|location=New York |
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|publisher=Academic Press, Inc. |
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|pages= 50–80 |
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|isbn=0-12-540028-4 |
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}}</ref> |
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==Biosynthesis and function== |
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] |
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The presence of queuine in certain tRNA is a nearly ubiquitous feature of eukaryotic life, meaning it is found in every healthy cell of the human body. It is also found in all other animals, plants, and fungi. The only known exception is brewer's yeast, ''Saccharomyces cerevisiae''. However, queuosine can be produced only by bacteria; higher organisms must obtain queuine from the diet, or salvage it from symbiotic microbes: a process for which dedicated enzymatic machinery exists.<ref>{{cite journal |
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| last1 = Zallot |
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| first1 = Rémi |
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| last2 = Brochier-Armanet |
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| first2 = Céline |
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| last3 = Gaston |
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| first3 = Kirk |
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| last4 = Forouhar |
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| first4 = Farhad |
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| last5 = Limbach |
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| first5 = Patrick |
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| last6 = Hunt |
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| first6 = John |
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| last7 = de Crécy-Lagard |
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| first7 = Valérie |
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| display-authors = 1 |
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| date = 15 August 2014 |
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| title = Plant, animal, and fungal micronutrient queuosine is salvaged by members of the DUF2419 protein family |
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| journal = ACS Chemical Biology |
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| volume = 9 |
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| issue = 8 |
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| pages = 1812–1825 |
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| doi = 10.1021/cb500278k |
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| pmid = 24911101 |
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| pmc = 4136680 |
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}}</ref> Because queuine is necessary for healthy cellular function in animals, but is produced exclusively by microbes, it can be considered a vitamin, akin to the ]—many which are also produced primarily or exclusively by bacteria.<ref>{{cite book |last1=Bjork |first1=Glenn |last2=Rasmusen |first2=Torgny |title=Modification and Editing of RNA |date=1998 |publisher=ASM Press |location=New York |page=480 |doi=10.1128/9781555818296.ch26 |url=https://onlinelibrary.wiley.com/doi/10.1128/9781555818296.ch26 |quote=Whereas bacteria can synthesize the precursor preQ0, eukaryotic organisms are unable to make queuine and have to rely on the presence of the base in the diet. Queuine can therefore be considered a vitamin.}}</ref> |
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The biosynthesis pathway for queuine shares a common enzymatic starting step with ]. Because queuosine in dietary or gut-bacterial RNA can be salvaged and converted to queuine by the human body, queuosine could be considered a ] of queuine. As of 2019, human queuine requirements are not well understood, and the prevalence of queuine deficiency in humans is unknown.<ref name="Skolnick2019">{{cite journal |
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] |
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| last1 = Skolnick |
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| first1 = Stephen |
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| last2 = Greig |
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| first2 = Nigel |
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| date = 1 March 2019 |
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| title = Microbes and monoamines: Potential neuropsychiatric consequences of dysbiosis |
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| url = https://www.cell.com/trends/neurosciences/fulltext/S0166-2236(18)30318-7 |
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| journal = Trends in Neurosciences |
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| volume = 42 |
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| issue = 3 |
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| pages = 151–163 |
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| doi = 10.1016/j.tins.2018.12.005 |
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| pmid = 30795845 |
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| s2cid = 72335336 |
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| access-date = 6 May 2020 |
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}}</ref> Plants obtain queuine from the tRNA of symbiotic bacteria in and around their roots. |
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Once salvaged, queuine replaces a guanine base in the anticodon of certain tRNAs, where it appears to play a role in ensuring rapid and accurate recognition of the corresponding ]s' codons. In the absence of queuosine modification, translation at Q-decoded codons slows down to the point that many proteins cannot fold properly.<ref>{{cite journal |
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| last1 = Tuorto |
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| first1 = Francesca |
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| last2 = Legrand |
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| first2 = Carine |
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| last3 = Cirzi |
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| first3 = Cansu |
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| last4 = Federico |
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| first4 = Guiseppina |
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| last5 = Liebers |
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| first5 = Reinhard |
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| last6 = Müller |
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| first6 = Martin |
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| last7 = Ehrenhofer-Murray |
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| first7 = Ann |
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| last8 = Dittmar |
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| first8 = Gunnar |
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| last9 = Gröne |
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| first9 = Hermann-Josef |
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| last10 = Lyko |
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| first10 = Frank |
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| display-authors = 1 |
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| date = 14 September 2018 |
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| title = Queuosine-modified tRNAs confer nutritional control of protein translation |
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| journal = EMBO J. |
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| volume = 37 |
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| issue = 18 |
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| pages = e99777 |
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| doi = 10.15252/embj.201899777 |
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| pmid = 30093495 |
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| pmc = 6138434 |
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}}</ref> |
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In animal experiments using "germ-free" mice, even the total absence of queuine in the diet is not lethal in the presence of an adequate supply of the dietary amino acid ]. Withdrawal of tyrosine from the diet, however, causes rapid physical deterioration and death over a period of two weeks. Tyrosine is not typically an essential nutrient for animals provided dietary phenylalanine, suggesting that queuine depletion impairs the activity of ]. |
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==Enzyme research== |
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BH<sub>4</sub> is a cofactor for the ] enzymes, which catalyze the conversion of ] to ], tyrosine to ], and ] to ], oxidizing BH<sub>4</sub> to ] (BH<sub>2</sub>) in the process. BH<sub>2</sub> must then be converted back to BH<sub>4</sub> by the enzyme ] before it can be used again. Queuine depletion appears to impair this "recycling" process, resulting in a deficit of BH<sub>4</sub> and an excess of BH<sub>2</sub>, which in turn impairs the activity of the aromatic amino acid hydroxylase enzymes.<ref>{{cite journal |
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| last1 = Rakovich |
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| first1 = Tatsiana |
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| last2 = Boland |
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| first2 = Coilin |
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| last3 = Bernstein |
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| first3 = Ilana |
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| last4 = Chikwana |
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| first4 = Vimbai |
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| last5 = Iwata-Reuyl |
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| first5 = Dirk |
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| last6 = Kelly |
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| first6 = Vincent |
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| display-authors = 1 |
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| date = 12 April 2011 |
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| title = Queuosine deficiency in eukaryotes compromises tyrosine production through increased tetrahydrobiopterin oxidation |
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| journal = Journal of Biological Chemistry |
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| volume = 286 |
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| issue = 22 |
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| pages = 19354–19363 |
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| doi = 10.1074/jbc.M111.219576 |
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| pmc=3103313 |
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| pmid = 9016755 |
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| doi-access = free |
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}}</ref> |
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Because the aromatic amino acid hydroxylase enzymes are the rate-limiting steps in the body's biosynthesis of ] and ] (and subsequent metabolites including ], ], and ]), queuine deficiency is under investigation as a potential cause of human diseases linked to a deficit of these neurotransmitters.<ref>{{cite journal |last1=Pennisi |first1=Elizabeth |title=Meet the Psychobiome |url=https://www.science.org/doi/10.1126/science.368.6491.570 |journal=Science |year=2020 |volume=368 |issue=6491 |pages=570–573 |doi=10.1126/science.368.6491.570 |pmid=32381701 |s2cid=218555010 |access-date=23 November 2022 |ref=Psychobiome}}</ref> |
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== References == |
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{{reflist}} |
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==External links== |
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* Human Metabolome Database: |
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] |
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] |
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