263254-55-3

Basic information

• Product Name: tert-butyl 2-(2-isobutyraMido-6-oxo-1H-purin-9(6H)-yl)acetate
• Synonyms: tert-butyl 2-(2-isobutyraMido-6-oxo-1H-purin-9(6H)-yl)acetate
• CAS NO: 263254-55-3
• Molecular Formula: C₁₅H₂₁N₅O₄
• Molecular Weight: 335.35834
• Mol File: 263254-55-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: tert-butyl 2-(2-isobutyraMido-6-oxo-1H-purin-9(6H)-yl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2-(2-isobutyraMido-6-oxo-1H-purin-9(6H)-yl)acetate(263254-55-3)
• EPA Substance Registry System: tert-butyl 2-(2-isobutyraMido-6-oxo-1H-purin-9(6H)-yl)acetate(263254-55-3)

Safety Data

• Hazardous Substances Data: 263254-55-3(Hazardous Substances Data)

Upstream product

• 5292-43-3 bromoacetic acid tert-butyl ester 
• 185610-53-1 N²-(isobutyryl-O⁶-diphenylcarbamoyl)guanine 
• 21047-89-2 2-N-isobutyrylguanine 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 118-00-3 G 
• 869657-57-8 N²-isobutyryl-7-(4-nitrobenzyl)guanine 
• 73-40-5 guanine 
• 21047-89-2 1,7-dihydro-2-(isobutyroyl)amino-6H-purin-6-one 
• 263254-48-4 [6-Diphenylcarbamoyloxy-2-(isobutyrylamino)purin-9-yl]acetic acid tert-butyl ester 

Downstream Products

• 864289-00-9 {[2-(4,5-dimethoxy-2-nitro-benzyloxycarbonylamino)-ethyl]-[(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-acetyl]-amino}-acetic acid tert-butyl ester 
• 172405-20-8 2-(2-isobutyramido-6-oxo-1H-purin-9(6H)-yl)acetic acid 

Relevant articles and documents

A convenient route to synthesize N2-(isobutyryl)-9-(carboxymethyl)guanine for aeg-PNA backbone

Synthesis of exclusive N2-(isobutyryl)-9-(carboxymethyl)guanine, an important moiety for peptide nucleic acid synthesis has been reported through a high-yielding reaction scheme starting from 6-chloro-2-amino purine. Crystal structures of two intermediates confirmed the formation of N9-regioisomer. This new synthetic route can potentially replace the conventional tedious method with moderate overall yield.

PNA-directed triple-helix formation by N7-xanthine

We report the first example of alkylation of underivatized xanthine with chloroacetic acid to yield a separable mixture of N7- and N 9-(methylenecarboxyl)xanthine and its conversion to a peptide nucleic acid monomer compatible with Fmoc-based oligomerization chemistry. Additionally, we have simultaneously prepared the N7- and N 9-PNA monomers of guanine by alkylation of 2-N-isobutyrylguanine which were subsequently separated. Molecular modeling of the nucleobase base triplets indicates that N7-xanthine and N7-guanine form isomorphous triplets with adenine and guanine, respectively. We also show that polyamides containing N7-xanthine are compatible with triple-helix formation. Georg Thieme Verlag Stuttgart.

Fmoc/Acyl protecting groups in the synthesis of polyamide (peptide) nucleic acid monomers

The chemical synthesis of polyamide (peptide) nucleic acid (PNA) monomers 22-25 has been accomplished using Fmoc [N-(2-aminoethyl)glycine backbone], anisoyl (adenine), 4-tert-butylbenzoyl (cytosine) and isobutyryl/ diphenylcarbamoyl (guanine) protecting-group combinations, thus allowing oligomer synthesis on both peptide and oligonucleotide synthesizers. An alternative method for the preparation of (N6-anisoyladenin-9-yl)acetic acid 7 is described using partial hydrolysis of a dianisoylated derivative. Different methods were studied for guanine alkylation including (a) Mitsunobu reaction; (b) low-temperature, sodium hydride- and (c) N, N-diisopropylethylaminemediated alkylation reactions to give preferentially N9-substituted derivatives. Empirical rules are proposed for differentiating N9/N7-substituted guanines based on their 13C NMR chemical-shift differences. The Royal Society of Chemistry 2000.