N2-Boc-guanine-9-acetic acid is a protected guanine derivative used in peptide nucleic acid (PNA) monomer synthesis and related nucleobase-conjugation chemistry. The exocyclic N2 amino group is Boc-protected, while the N9-acetic-acid side chain provides a carboxyl handle for amide-bond formation.

This dual protection/functionalization pattern makes the compound useful when a guanine nucleobase must be incorporated into a PNA backbone or attached to an amine-containing linker without uncontrolled reaction at the guanine exocyclic amino group.

Product Information

Role in PNA Monomer Synthesis

Peptide nucleic acids use a peptide-like backbone rather than the sugar-phosphate backbone of DNA or RNA. Guanine-containing PNA monomers therefore require a protected guanine unit that can be coupled to a suitable backbone precursor. N2-Boc-guanine-9-acetic acid provides that protected nucleobase plus a carboxylic-acid coupling handle in one reagent.

Coupling and Protecting-Group Logic

The Boc group protects the guanine N2 amino function during coupling, while the acetic-acid group attached at N9 can be activated using standard amide-forming chemistry. Reagent selection, base and reaction time should be optimized to preserve nucleobase integrity and minimize side reactions.

Applications Beyond PNA

In addition to PNA monomer preparation, this building block can be used in nucleobase-linker synthesis, guanine-containing molecular probes and research conjugates where a protected guanine unit is attached through an amide bond. It is not itself a DNA/RNA nucleotide and should not be described as a direct oligonucleotide monomer.

Downstream Research Use

After incorporation into a PNA or conjugate and appropriate deprotection/purification, the final construct may be evaluated in hybridization, binding, molecular-recognition, cell-based delivery or other nucleic-acid research assays. The protected building block itself is intended for synthesis rather than direct biological testing.

Product Documents

A Material Safety Data Sheet (MSDS) is available for this product to support laboratory handling, storage and safety assessment.

MSDS_N2-Boc-guanine-9-acetic acid_AS4054

Frequently Asked Questions

Is N2-Boc-guanine-9-acetic acid a PNA building block?

Yes. It is commonly used as a protected guanine precursor in the synthesis of guanine-containing PNA monomers.

What is protected by the Boc group?

The exocyclic N2 amino group of guanine is Boc-protected to control reactivity during coupling chemistry.

What functional group is used for coupling?

The N9-acetic-acid substituent provides a carboxyl group that can be activated for amide-bond formation.

Related Technical Resources

Browse Specialty Peptide Building Blocks or contact Alan Scientific for Custom Chemical and Peptide Synthesis.

Research Use Only.