149376-67-0

Usage

Uses

Used in Biochemical Research:
9H-Purine-9-acetic acid, 6-[[(phenylmethoxy)carbonyl]amino]is employed as a research compound for its potential applications in the field of biochemistry. Its unique structure allows scientists to explore its interactions with biological systems and its potential as a therapeutic agent.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 9H-Purine-9-acetic acid, 6-[[(phenylmethoxy)carbonyl]amino]is used as a lead compound for the development of new drugs. Its complex structure may offer insights into the design of novel therapeutics, particularly in the area of purine-based medications.
Used in Drug Discovery:
9H-Purine-9-acetic acid, 6-[[(phenylmethoxy)carbonyl]amino]is utilized in drug discovery processes to identify new molecular targets and pathways. Its properties may contribute to the development of innovative treatments for various diseases and conditions.

Upstream product

• 25477-96-7 ethyl 2-(9H-adenin-9-yl)acetate 
• 66224-66-6 adenine 
• 543-27-1 isobutyl chloroformate 
• 501-53-1 benzyl chloroformate 
• 82892-54-4 1-(benzyloxycarbonyl)-3-ethylimidazolium tetrafluoroborate 
• 149376-66-9 ethyl (N⁶-(benzyloxycarbonyl)adenin-9-yl)acetate 
• 82919-04-8 (N⁶-benzyloxycarbonyl)adenine 
• 212143-41-4 methyl N⁶-carbobenzoxy-2-(6-amino-9H-purin-9-yl)acetate 

Downstream Products

• 255735-96-7 rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-N⁶-benzyloxycarbonyl-adeninacetyl-amino]-ortho-chlorophenylacetic acid-(cyclohexen-1-yl)-amide 
• 625442-91-3 N-(2-pentacosa-10,12-diynoylaminoethyl)-N-(N⁶-(benzyloxycarbonyl)adenin-9-ylacetyl)glycine methyl ester 
• 886208-35-1 methyl N^α-[[6-N-(benzyloxycarbonyl)adenin-9-yl]acetyl]-N^G-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-sulfonyl)-L-argininate 
• 172729-75-8 N₆-(benzyloxycarbonyl)-9-(chlorocarbonylmethyl)adenine 
• 1050504-36-3 [(3S,4R)-1-[2-[6-(benzyloxycarbonylamino)-9H-purin-9-yl]acetyl]-4-(t-butoxycarbonylamino)pyrrolidin-3-yl]-methyl benzoate 
• 193621-92-0 [[2-(6-Benzyloxycarbonylamino-purin-9-yl)-acetyl]-((1S,2S)-2-tert-butoxycarbonylamino-cyclohexyl)-amino]-acetic acid ethyl ester 
• 171855-77-9 N-(carbamoylmethyl)-N-(N⁶-(benzyloxycarbonyl)adenin-9-ylacetyl)-β-alanine ethyl ester 
• 149376-68-1 ethyl N-((N⁶-(benzyloxycarbonyl)adenin-9-yl)acetyl)-N-(2-Boc-aminoethyl)glycinate 
• 1432025-43-8 C₄₈H₄₈N₁₈O₈ 
• 1372404-64-2 C₅₀H₆₁N₁₇O₁₄S₂ 
• 1352089-45-2 N-(6,9-dihydro-9-(15-(tert-butoxycarbonyl)-3-(2-(2-(morpholin-4-yl)ethylamino)-2-oxoethyl)-2,7,13,19-tetraoxo-21-phenyl-9-(2-((6-phenylmethoxycarbonylamino)-9H-purin-9-yl)acetyl)-20-oxa-3,6,9,12,15,18-hexaazaheneicos-1-yl)-6-oxo-1H-purin-2-yl)carbamic acid phenylmethyl ester 
• 1349193-21-0 N-[N₆-(benzyloxycarbonyl)adenin-9-ylacetyl]-N-(propyn-3-yl)glycine ethyl ester 
• 1118531-58-0 C₄₇H₅₆N₁₀O₁₁ 

Relevant academic research and scientific papers

Experimental study of hydrogen bonding potentially stabilizing the 5'-deoxyadenosyl radical from coenzyme B12

Coenzyme B12 can assist radical enzymes that accomplish the vicinal interchange of a hydrogen atom with a functional group. It has been proposed that the Co-C bond homolysis of coenzyme B12 to cob(II)alamin and the 5'-deoxyadenosyl radical is aided by hydrogen bonding of the corrin C19-H to the 3'-O of the ribose moiety of the incipient 5'-deoxyadenosyl radical, which is stabilized by 30 kJ mol-1 (B. Durbeej et al., Chem. Eur. J. 2009, 15, 8578-8585). The diastereoisomers (R)- and (S)-2,3-dihydroxypropylcobalamin were used as models for coenzyme B 12. A downfield shift of the NMR signal for the C19-H proton was observed for the (R)-isomer (Δ=4.45 versus 4.01 ppm for the (S)-isomer) and can be ascribed to an intramolecular hydrogen bond between the C19-H and the oxygen of CHOH. Crystal structures of (R)- and (S)-2,3-dihydroxypropylcobalamin showed C19-H···O distances of 3.214(7) A? (R-isomer) and 3.281(11) A? (S-isomer), which suggest weak hydrogen-bond interactions (-ΔG-1) between the CHOH of the dihydroxypropyl ligand and the C19-H. Exchange of the C19-H, which is dependent on the cobalt redox state, was investigated with cob(I)alamin, cob(II)alamin, and cob(III)alamin by using NMR spectroscopy to monitor the uptake of deuterium from deuterated water in the pH range 3-11. No exchange was found for any of the cobalt oxidation states. 3',5'-Dideoxyadenosylcobalamin, but not the 2',5'-isomer, was found to act as a coenzyme for glutamate mutase, with a 15-fold lower kcat/KM than 5'-deoxyadenosylcobalamin. This indicates that stabilization of the 5'-deoxyadenosyl radical by a hydrogen bond that involves the C19-H and the 3'-OH group of the cofactor is, at most, 7 kJ mol-1 (-ΔG). Examination of the crystal structure of glutamate mutase revealed additional stabilizing factors: hydrogen bonds between both the 2'-OH and 3'-OH groups and glutamate 330. The actual strength of a hydrogen bond between the C19-H and the 3'-O of the ribose moiety of the 5'-deoxyadenosyl group is concluded not to exceed 6 kJ mol-1 (-ΔG).

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 2,6-diaminopurine nucleobases

A novel class of compounds, known as peptide nucleic acids, bind complementary DNA and RNA strands more strongly than a corresponding DNA strand, and exhibit increased sequence specificity and binding affinity. The peptide nucleic acids of the invention comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases attached to a polyamide backbone. Some PNAs of the invention also contain C1-C8alkylamine side chains.

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 more strongly than a corresponding DNA strand, and exhibit 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 attached to a polyamide backbone, and contain C1 -C8 alkylamine side chains. Methods of enhancing the solubility, binding affinity and sequence specificity of PNAs are provided.

Peptide nucleic acids having amino acid side chains

A novel class of compounds, known as peptide nucleic acids, bind complementary DNA and RNA strands more strongly than the corresponding DNA or RNA strands, and exhibit 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 attached to a polyamide backbone, and contain alkylamine side chains.

Fmoc Mediated Synthesis of Peptide Nucleic Acids.

The syntheses of the Fmoc-protected Peptide Nucleic Acid (PNA) monomer pentafluorophenyl esters of adenine (26), cytosine (23), guanine (29) and thymine (20), and their oligomerization are described.The Fmoc PNA backbone 1 is prepared as a stable hydrochl

Synthesis of Peptide Nucleic Acid Monomers Containing the Four Natural Nucleobases: Thymine, Cytosine, Adenine, and Guanine and Their Oligomerization

The preparation of mixed-sequence PNAs (PNAs containing the four natural nucleobases; thymine, cytosine, adenine, and guanine) is described.The PNA monomers containing thymine, Cbz-protected cytosine, or adenine or benzyl-protected guanine were prepared v

Peptide Nucleic Acids containing Adenine or Guanine recognize Thymine and Cytosine in Complementary DNA Sequences

Peptide nucleic acid (PNA) monomer building blocks for the introduction of G and A are prepared and used to synthesise H-T4XT5-Lys-NH2 (X=G or A), which are shown by Tm measurements to recognize their complementary DNA sequences in both the parallel (N-te