144564-95-4

Basic information

• Product Name: [N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid
• Synonyms: [N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid
• CAS NO: 144564-95-4
• Molecular Weight: 303.274
• Mol File: 144564-95-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 272-274 °C(Solv: methanol (67-56-1))
• Density: 1.39±0.1 g/cm3(Predicted)
• CAS DataBase Reference: [N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid(144564-95-4)
• EPA Substance Registry System: [N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid(144564-95-4)

Safety Data

• Hazardous Substances Data: 144564-95-4(Hazardous Substances Data)

Usage

Description

[N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid is a chemical compound that features a cytosine-1-yl group connected to an acetic acid via a linker molecule. [N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid is characterized by the presence of a protective benzyloxy carbonyl group attached to the cytosine-1-yl group, which plays a crucial role in the synthesis of various biologically active molecules and nucleoside derivatives.

Uses

Used in Pharmaceutical and Chemical Biology Research:
[N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid is utilized as a building block in the synthesis of nucleoside analogs, which are essential for the development of new pharmaceuticals and chemical biology research. The benzyloxy carbonyl group ensures the stability of the cytosine-1-yl group during the chemical synthesis process, allowing for selective deprotection when necessary to expose the reactive group for further reactions.
Used in Drug Discovery:
As a valuable chemical intermediate, [N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid contributes to the advancement of drug discovery by enabling the creation of novel nucleoside derivatives with potential therapeutic applications. [N⁴-[(benzyloxy)carbonyl]cytosine-1-yl]acetic acid's unique structure and protective group facilitate the development of new molecules with improved pharmacological properties and targeted effects on specific biological pathways.

Upstream product

• 28230-32-2 3-hydroxy-3,4-dihydrobenzotriazine-4-one 
• 55175-48-9 ethyl 2-(4-amino-2-oxopyrimidin-1(2H)-yl)acetate 
• 501-53-1 benzyl chloroformate 
• 212143-40-3 (N⁴-(benzyloxycarbonyl)cytosin-1-yl)acetic acid methyl ester 
• 96-32-2 bromoacetic acid methyl ester 
• 149411-91-6 N-benzyloxycarbonyl cytosine 
• 186046-91-3 methyl (cytosine-1-yl)acetate 

Downstream Products

• 193621-93-1 [[2-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-((1S,2S)-2-tert-butoxycarbonylamino-cyclohexyl)-amino]-acetic acid ethyl ester 
• 1050504-34-1 [(3S,4R)-1-[2-[4-(benzyloxycarbonylamino)-2-oxopyrimidin-1(2H)-yl]acetyl]-4-(t-butoxycarbonylamino)-pyrrolidin-3-yl]methyl benzoate 
• 622367-01-5 (1-{[[1-(2-tert-butoxycarbonylamino-ethylcarbamoyl)-3-methyl-butyl]-(3-methyl-butyl)-carbamoyl]-methyl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-carbamic acid benzyl ester 
• 399564-83-1 {(2-allyloxycarbonylamino-benzyl)-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid tert-butyl ester 
• 345201-71-0 {(2-allyloxycarbonylamino-benzyl)-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid methyl ester 
• 221555-26-6 {[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-[2-(2-{[2-(6-tert-butoxycarbonylamino-hexanoylamino)-ethyl]-[(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetylamino)-ethyl]-amino}-acetic acid methyl ester 
• 221555-25-5 [[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-(2-{2-[[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-(2-tert-butoxycarbonylamino-ethyl)-amino]-acetylamino}-ethyl)-amino]-acetic acid methyl ester 
• 221554-98-9 C₆₀H₆₉N₁₅O₁₈ 
• 189215-92-7 (2S,4R)-1-[2-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidine-2-carboxylic acid methyl ester 
• 149035-03-0 N⁴-(Z)-1-(carboxymethyl)cytosine pentafluorophenyl ester 
• 938175-07-6 ethyl N-((N-⁴-(benzyloxycarbonyl)cytosin-1-yl)acetyl)-N-(2-Boc-aminoethyl)glycinate 

Relevant articles and documents

Peptide Nucleic Acid with Double Face: Homothymine-Homocytosine Bimodal Cα-PNA (bm-Cα-PNA) Forms a Double Duplex of the bm-PNA2:DNA Triplex

Cα-bimodal peptide nucleic acids (bm-Cα-PNA) are PNAs with two faces and are designed homologues of PNAs in which each aminoethylglycine (aeg) repeating unit in the standard PNA backbone hosts a second nucleobase at Cα through a spacer chain with a triazole linker. Such bm-Cα-PNA with mixed sequences can form double duplexes by simultaneous binding to two complementary DNAs, one to the base sequence on t-amide side and the other to the bases on the Cα side chain. The synthesis of bm-Cα-PNA with homothymine (T7) on the t-amide face and homocytosine (C5) on the Cα side chain through the triazole linker was achieved by solid phase synthesis with the global click reaction. In the presence of complementary DNAs dA8 and dG6 at neutral pH, bm-Cα-PNA 1 forms a higher order pentameric double duplex of a triplex composed of two bm-Cα-PNA-C5:dG5 duplexes built on a core (bm-Cα-PNA-T7)2:dA8 triplex. Circular dichroism studies showed that assembly can be achieved by either triplex first and duplex later or vice versa. Isothermal titration calorimetry data indicated that the assembly is driven by favorable enthalpy. These results validate concurrent multiple complex formation by bimodal PNAs with additional nucleobases at Cα or Cγon the aeg-PNA backbone and open up ways to design programmed supramolecular assemblies.

NEW SYNTHONS FOR THE SYNTHESIS OF CHIRAL PEPTIDE NUCLEIC ACIDS AND METHODS FOR PREPARING THE SAME

Novel l-acyl-3-amino-4-hydroxymethylpyiτolidine derivatives useful as PNA synthons optionally having protecting groups suitable of removal under mild conditions are disclosed having the formula (E) wherein: R1 is H or R-C(=O), wherein R is stra

Peptide nucleic acids having enhanced binding affinity, sequence specificity and solubility

A novel class of compounds known as peptide nucleic acids, bind complementary DNA and RNA strands, and generally do so more strongly than the corresponding DNA or RNA strands while exhibiting increased sequence specificity and solubility. The peptide nucleic acids comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases, including 2,6-diaminopurine, attached to a polyamide backbone, and contain alkyl amine side chains.