1354832-42-0

Basic information

• Product Name: 2-(2,6-bis(bis(tert-butoxycarbonyl)aMino)-9H-purin-9-yl)acetic acid
• Synonyms: 2-(2,6-bis(bis(tert-butoxycarbonyl)aMino)-9H-purin-9-yl)acetic acid;2-(2,6-diaMino-9H-purin-9-yl)acetic acid (with 4 boc-protecting groups);2-(2,6-diamino-9H-purin-9-yl)acetic acid
• CAS NO: 1354832-42-0
• Molecular Formula: C₂₇H₄₀N₆O₁₀
• Molecular Weight: 608.6407
• Mol File: 1354832-42-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 685.6±65.0 °C(Predicted)
• Appearance: /
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.47±0.10(Predicted)
• CAS DataBase Reference: 2-(2,6-bis(bis(tert-butoxycarbonyl)aMino)-9H-purin-9-yl)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,6-bis(bis(tert-butoxycarbonyl)aMino)-9H-purin-9-yl)acetic acid(1354832-42-0)
• EPA Substance Registry System: 2-(2,6-bis(bis(tert-butoxycarbonyl)aMino)-9H-purin-9-yl)acetic acid(1354832-42-0)

Safety Data

• Hazardous Substances Data: 1354832-42-0(Hazardous Substances Data)

Usage

General Description

2-(2,6-bis(bis(tert-butoxycarbonyl)amino)-9H-purin-9-yl)acetic acid is a chemical compound with the molecular formula C22H31N7O8. It is an amino acid derivative with two tert-butoxycarbonyl protecting groups attached to the amino groups of a purine base. 2-(2,6-bis(bis(tert-butoxycarbonyl)aMino)-9H-purin-9-yl)acetic acid is commonly used as a reagent in peptide synthesis and organic chemistry research. It is also used as a building block in the synthesis of various pharmaceuticals and bioactive compounds. Additionally, it has potential applications in the development of nucleic acid analogues and other biologically active molecules.

Upstream product

• 1904-98-9 2,6-diaminopurine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1354832-41-9 benzyl N₂,N₂,N₆,N₆-tetra(Boc)-2,6-diaminopurin-9-ylacetate 
• 1354832-40-8 N₂,N₂,N₆,N₆-tetra(Boc)-2,6-diamino-9H-purine 
• 1354832-39-5 9,N₂,N₂,N₆,N₆-penta(Boc)-2,6-diaminopurine 

Relevant articles and documents

Incorporation of Pseudo-complementary Bases 2,6-Diaminopurine and 2-Thiouracil into Serinol Nucleic Acid (SNA) to Promote SNA/RNA Hybridization

Serinol nucleic acid (SNA) is a promising candidate for nucleic acid-based molecular probes and drugs due to its high affinity for RNA. Our previous work revealed that incorporation of 2,6-diaminpurine (D), which can form three hydrogen bonds with uracil, into SNA increases the melting temperature of SNA-RNA duplexes. However, D incorporation into short self-complementary regions of SNA promoted self-dimerization and hindered hybridization with RNA. Here we synthesized a SNA monomer of 2-thiouracil (sU), which was expected to inhibit base pairing with D by steric hindrance between sulfur and the amino group. To prepare the SNA containing D and sU in high yield, we customized the protecting groups on D and sU monomers that can be readily deprotected under acidic conditions. Incorporation of D and sU into SNA facilitated stable duplex formation with target RNA by suppressing the self-hybridization of SNA and increasing the stability of the heteroduplex of SNA and its complementary RNA. Our results have important implications for the development of SNA-based probes and nucleic acid drugs.

Synthesis and oligomerization of Fmoc/Boc-protected PNA monomers of 2,6-diaminopurine, 2-aminopurine and thymine

A Boc-protecting group strategy for Fmoc-based PNA (peptide nucleic acid) oligomerization has been developed for thymine, 2,6-diaminopurine (DAP) and 2-aminopurine (2AP). The monomers may be used interchangeably with standard Fmoc PNA monomers. The DAP monomer was incorporated into a PNA and was found to selectively bind to T (ΔTm ≥ +6 °C) in a complementary DNA strand. The 2AP monomer showed excellent discrimination of T (ΔT m ≥ +12 °C) over the other nucleobases. 2AP also acted as a fluorescent probe of the PNA:DNA duplexes and displayed fluorescence quenching dependent on the opposite base.