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Nucleoside Q, also known as 7-deazaguanosine, is a modified nucleoside located in the anticodon wobble position of specific tRNAs. It is found in tRNA that has an additional cyclopentenyl ring added via an NH group to the methyl group of 7-methyl-7-deazaguanosine. This cyclopentenyl ring may carry other substituents. Nucleoside Q and its derivatives typically replace guanosine in the anticodon of tRNAsGUN of eubacteria and in cytoplasmic and mitochondrial tRNAs of some eukaryotes. It is produced from GTP (G837905) via the 7-deazaguanosine (D201390) precursor in bacteria.

57072-36-3

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57072-36-3 Usage

Uses

Used in Molecular Biology:
Nucleoside Q is used as a modified nucleoside in tRNA for [application reason its role in the anticodon wobble position, which may have implications for protein synthesis and genetic information transfer].
Used in Bacterial Systems:
In bacteria, Nucleoside Q is used as a precursor for the production of 7-deazaguanosine (D201390) from GTP (G837905) for [application reason its involvement in the biosynthesis of essential biomolecules in bacterial cells].
Used in Eukaryotic Systems:
Nucleoside Q is used as a replacement for guanosine in the anticodon of tRNAsGUN of eukaryotes for [application reason its potential role in the regulation of protein synthesis and genetic information transfer in both cytoplasmic and mitochondrial tRNAs of eukaryotic cells].

Check Digit Verification of cas no

The CAS Registry Mumber 57072-36-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,7,0,7 and 2 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 57072-36:
(7*5)+(6*7)+(5*0)+(4*7)+(3*2)+(2*3)+(1*6)=123
123 % 10 = 3
So 57072-36-3 is a valid CAS Registry Number.
InChI:InChI=1/C17H23N5O7/c18-17-20-14-10(15(28)21-17)6(3-19-7-1-2-8(24)11(7)25)4-22(14)16-13(27)12(26)9(5-23)29-16/h1-2,4,7-9,11-13,16,19,23-27H,3,5H2,(H3,18,20,21,28)/t7-,8-,9+,11+,12+,13+,16+/m0/s1

57072-36-3Downstream Products

57072-36-3Relevant academic research and scientific papers

SYNTHESES OF HYPERMODIFIED NUCLEOSIDE Q, AND ITS BIOSYNTHETIC PRECURSORS PREQ0 AND PREQ1

Kondo, Tadao,Okamoto, Kaoru,Ohgi, Tadaaki,Goto, Toshio

, p. 207 - 213 (1986)

The nucleoside Q (1) and its biosynthetic precursors, preQ0 (2) and preQ1 (3) were synthesized from the key intermediate, 6-bromo-2-diacetylamino-3,4-dihydro-3-methoxymethyl-5-methyl-7-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-7H-pyrrolopyrimidin-4-one (6) by conversion of the methyl group on the base to 3S,4R,5S-4,5-dihydroxycyclopent-1-en-3-ylaminomethyl, cyano, and aminomethyl groups, respectively.

Synthesis of the transfer-RNA nucleoside queuosine by using a chiral allyl azide intermediate

Klepper, Florian,Jahn, Eva-Maria,Hickmann, Volker,Carell, Thomas

, p. 2325 - 2327 (2008/03/11)

Chilled out: Chiral allyl azides are rarely used in natural product synthesis because of their tendency to undergo a [3.3] sigmatropic rearrangement (see scheme, top). In allylic cyclopentenyl azides, this rearrangement can be suppressed at just 0°C, enabling a short convergent synthesis of the hypermodified transfer-RNA nucleoside queuosine. (Chemical Equation Presented).

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