149376-67-0

Basic information

• Product Name: 9H-Purine-9-acetic acid, 6-[[(phenylmethoxy)carbonyl]amino]-
• Synonyms: N6-Cbz-adenin-9-ylacetic acid
• CAS NO: 149376-67-0
• Molecular Formula: C15H13N5O4
• Molecular Weight: 327.299
• Mol File: 149376-67-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 9H-Purine-9-acetic acid, 6-[[(phenylmethoxy)carbonyl]amino]-(CAS DataBase Reference)
• NIST Chemistry Reference: 9H-Purine-9-acetic acid, 6-[[(phenylmethoxy)carbonyl]amino]-(149376-67-0)
• EPA Substance Registry System: 9H-Purine-9-acetic acid, 6-[[(phenylmethoxy)carbonyl]amino]-(149376-67-0)

Safety Data

• Hazardous Substances Data: 149376-67-0(Hazardous Substances Data)

Usage

General Description

9H-Purine-9-acetic acid, 6-[[(phenylmethoxy)carbonyl]amino]-, is a chemical compound with a complex structure. The chemical formula for this compound is C17H15N5O4. It belongs to the class of organic compounds known as purine nucleosides, which are compounds comprising a purine base attached to a sugar. Its side chain features a phenylmethoxy group and a carbonyl amino group, which differentiates it from other similar compounds. 9H-Purine-9-acetic acid, 6-[[(phenylmethoxy)carbonyl]amino]- is mainly used in biochemical research and is not naturally occurring. Due to its complex structure, it may exhibit a variety of chemical and biological properties that may be of significance in medicinal chemistry.

Upstream product

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

Downstream Products

• 149376-69-2 N-((N⁶-(benzyloxycarbonyl)adenin-9-yl)acetyl)-N-(2-Boc-aminoethyl)glycine 
• 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 
• 1050504-36-3 [(3S,4R)-1-[2-[6-(benzyloxycarbonylamino)-9H-purin-9-yl]acetyl]-4-(t-butoxycarbonylamino)pyrrolidin-3-yl]-methyl benzoate 
• 172729-75-8 N₆-(benzyloxycarbonyl)-9-(chlorocarbonylmethyl)adenine 
• 171855-78-0 N-(N-tert-butyloxycarbonylaminomethyl)-N-(N⁹-benzyloxycarbonyladenin-9-ylacetyl)-β-alanine ethyl ester 
• 171855-80-4 N-(N-tert-butyloxycarbonylaminomethyl)-N-(N⁹-benzyloxycarbonyladenin-9-ylacetyl)-β-alanine 
• 399564-98-8 {[2-(2-{[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-benzyl]-amino}-acetylamino)-benzyl]-[(6-benzyloxycarbonylamino-purin-9-yl)-acetyl]-amino}-acetic acid tert-butyl ester 
• 399564-92-2 {(2-amino-benzyl)-[(6-benzyloxycarbonylamino-purin-9-yl)-acetyl]-amino}-acetic acid tert-butyl ester 
• 676555-58-1 6-{2-[[(2-amino-6-benzyloxy-purin-9-yl)-acetyl]-(2-{2-[[(6-benzyloxycarbonylamino-purin-9-yl)-acetyl]-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-ethyl)-amino]-acetylamino}-ethyl)-amino]-acetylamino}-hexanoic acid tert-butyl ester 
• 676555-67-2 [[2-(2-Amino-6-benzyloxy-purin-9-yl)-acetyl]-(2-{2-[[2-(6-benzyloxycarbonylamino-purin-9-yl)-acetyl]-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-ethyl)-amino]-acetylamino}-ethyl)-amino]-acetic acid methyl ester 

Relevant articles and documents

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).

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 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.