3768-18-1 Usage
Description
N4-Acetylcytidine is a modified nucleoside and endogenous urinary nucleoside product of the degradation of tRNA. It is a biological marker for various cancers with elevated concentrations present in urine, as tRNA is excreted in abnormal amounts in the urine of cancer patients. N4-Acetylcytidine is also a partially protected cytidine and can be used as a synthetic building block to prepare further derivatized nucleosides such as 2',3'-dideoxycytidine.
Uses
Used in Medical Applications:
N4-Acetylcytidine is used as a biomarker for the diagnosis of various cancers, as it is present in elevated concentrations in the urine of cancer patients. The abnormal excretion of tRNA in the urine of cancer patients makes N4-Acetylcytidine a valuable tool in cancer detection and monitoring.
Used in Inflammation-Related Disease Diagnosis:
N4-Acetylcytidine is used as a nucleotide-derived metabolite for the diagnosis of inflammation-related diseases. Its presence in urine can help in identifying and monitoring the progression of such diseases.
Used in Pharmaceutical Industry:
N4-Acetylcytidine is used as a synthetic building block in the preparation of further derivatized nucleosides, such as 2',3'-dideoxycytidine. This makes it a valuable component in the development of new drugs and therapies for various medical conditions.
Biosynthesis
N4-acetylcytidine (ac4C) is a post-transcriptional modification of RNA that is conserved across all domains of life. All characterized sites of ac4C in eukaryotic RNA occur in the central nucleotide of a 5’-CCG-3’ consensus sequence. However, the thermodynamic consequences of cytidine acetylation in this context have never been assessed due to its challenging synthesis. Here we report the synthesis and biophysical characterization of ac4C in its endogenous eukaryotic sequence context. First, we develop a synthetic route to homogenous RNAs containing electrophilic acetyl groups. Next, we use thermal denaturation to interrogate the effects of ac4C on duplex stability and mismatch discrimination in a native sequence found in human ribosomal RNA. Finally, we demonstrate the ability of this chemistry to incorporate ac4C into the complex modification landscape of human tRNA, and use duplex melting combined with sequence analysis to highlight a potentially unique enforcing role for ac4C in this setting. By enabling the analysis of nucleic acid acetylation in its physiological sequence context, these studies establish a chemical foundation for understanding the function of a universally-conserved nucleobase in biology and disease.Site-Specific Synthesis of N4-Acetylcytidine in RNA Reveals Physiological Duplex Stabilizationhttps://www.biorxiv.org/content/10.1101/2021.11.12.468326v1.full.pdf
Check Digit Verification of cas no
The CAS Registry Mumber 3768-18-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,7,6 and 8 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 3768-18:
(6*3)+(5*7)+(4*6)+(3*8)+(2*1)+(1*8)=111
111 % 10 = 1
So 3768-18-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H15N3O6/c1-5(16)12-7-2-3-14(11(19)13-7)10-9(18)8(17)6(4-15)20-10/h2-3,6,8-10,15,17-18H,4H2,1H3,(H,12,13,16,19)/t6-,8-,9-,10-/m1/s1
3768-18-1Relevant articles and documents
A convenient synthesis of N4,O3′,O 5′-triacetyl-2′-ketocytidine
Kjell, Douglas P.,Slattery, Brian J.
, p. 469 - 474 (1997)
A convenient synthesis of the title compound in four steps from cytidine is reported. Key transformations include differentiation of the 2' position as N4,O3′,O5′ triacetyl-2,2′-anhydrocytidine, opening to the arabino derivative, and oxidation of the 2′ position with the Dess-Martin reagent. Copyright
Phosphonate analogues of cytosine arabinoside monophosphate
Chen, Xuemei,Jung, Kang-Yeoun,Wiemer, David F.,Wiemer, Andrew J.,Hohl, Raymond J.
, p. 1783 - 1786 (2002)
Phosphonate derivatives of cytidine and cytosine arabinoside have been prepared from the corresponding nucleoside aldehydes and tested for their ability to serve as substrates for nucleotide monophosphate kinase and for their toxicity to K562 leukemia cells.
Stereoselective synthesis of the 5′-hydroxy-5′-phosphonate derivatives of cytidine and cytosine arabinoside
Chen, Xuemei,Wiemer, Andrew J.,Hohl, Raymond J.,Wiemer, David F.
, p. 9331 - 9339 (2002)
Both the (R)- and (S)-5′-hydroxy 5′-phosphonate derivatives of cytidine and cytosine arabinoside (ara-C) have been prepared via phosphite addition or a Lewis acid mediated hydrophosphonylation of appropriately protected 5′-nucleoside aldehydes. Phosphite addition to a cytosine aldehyde protected as the 2′,3′-acetonide gave predominately the 5′R isomer, while phosphite addition to the corresponding 2′,3′-bis TBS derivative favored the 5′S stereochemistry. In contrast, phosphite addition to the 2′,3′-bis TBS protected aldehyde derived from ara-C gave only the 5′R adduct. However, TiC4-mediated hydrophosphonylation of the same ara-C aldehyde favored the 5′S stereoisomer by a 2:1 ratio. Once all four of the diastereomers were in hand, the stereochemistry of these compounds could be assigned based on their spectral data or that obtained from their O-methyl mandelate derivatives. After hydrolysis of the phosphonate esters and various protecting groups, the four α-hydroxy phosphonic acids were tested for their ability to serve as substrates for the enzyme nucleoside monophosphate kinase and for their toxicity to K562 cells.
An efficient one-pot N-acylation of deoxy- and ribo-cytidine using carboxylic acids activated in situ with 2-chloro-4,6-dimethoxy-1,3,5-triazine
Rode, Ambadas B.,Son, Sang Jun,Hong, In Seok
experimental part, p. 2061 - 2064 (2010/11/19)
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Electron-deficient benzotriazoles for the selective N-acetylation of nucleosides
Reid, Andrew K.,McHugh, Callum J.,Richie, Graham,Graham, Duncan
, p. 4201 - 4203 (2007/10/03)
The use of an acetylated benzotriazole for the selective protection of the amino groups of cytidine and 2′-deoxycytidine is reported. The use of the acetyl group is of considerable interest industrially in this role, and a single-step protection strategy advantageous in bulk production. 1-Acetyl-4-nitrobenzotriazole was found to readily acetylate the amine of cytidine preferentially over the exposed alcohol functionalities. With adaptation of the protocol, 2′-deoxycytidine was protected using the same reagent. A similar approach was attempted for the benzoylation of adenosine but was found to be unsuitable.
