Fmoc-PNA-C(Bhoc)-OH is a protected peptide nucleic acid monomer featuring Bhoc protection on the nucleobase. The residue supports PNA backbone construction for hybridization studies and biophysical modeling. Researchers apply it to test synthetic strategies and nucleic acid mimicry. Its dual protection enhances design flexibility.
CAT No: R2102
CAS No:186046-81-1
Synonyms/Alias:Fmoc-PNA-C(Bhoc)-OH;186046-81-1;2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid;MFCD22373799;2-[[2-[4-(benzhydryloxycarbonylamino)-2-oxopyrimidin-1-yl]acetyl]-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]amino]acetic acid;2-[N-[2-(Fmoc-amino)ethyl]-2-[4-[[(benzhydryloxy)carbonyl]amino]-2-oxopyrimidin-1(2H)-yl]acetamido]acetic Acid;SCHEMBL14308494;DTXSID201101881;BCP10640;LHA04681;HY-W540122;SB60461;AC-37007;BS-49835;N-[[4-[[(diphenylmethoxy)carbonyl]amino]-2-oxo-1(2h)-pyrimidinyl]acetyl]-n-[2-[[(9h-fluoren-9-ylmethoxy)carbonyl]amino]ethyl]glycine;SY253674;CS-0621853;D5932;F19155;[2-(4-{[(diphenylmethoxy)carbonyl]amino}-2-oxopyrimidin-1-yl)-N-(2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethyl)acetamido]acetic acid;2-[2-(4-{[(diphenylmethoxy)carbonyl]amino}-2-oxo-1,2-dihydropyrimidin-1-yl)-N-[2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)ethyl]acetamido]acetic acid;N-[2-[4-[[(Diphenylmethoxy)carbonyl]amino]-2-oxo-1(2H)-pyrimidinyl]acetyl]-N-[2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]ethyl]glycine;
Fmoc-PNA-C(Bhoc)-OH is a synthetic monomer designed for the solid-phase synthesis of peptide nucleic acids (PNAs), a class of DNA analogues characterized by a pseudopeptide backbone. This compound features an Fmoc-protected amino terminus and a Bhoc-protected cytosine base, enabling precise incorporation of cytosine residues during automated or manual assembly of PNA oligomers. Its structure is optimized for compatibility with standard peptide synthesis protocols, making it an essential building block in the development of sequence-specific PNA probes and functional biopolymers. The unique properties of PNAs, such as high binding affinity and specificity to complementary nucleic acid sequences, underpin the research significance of this monomer in molecular biology, diagnostics, and biotechnological innovation.
PNA synthesis: The primary application of Fmoc-PNA-C(Bhoc)-OH lies in the stepwise assembly of PNA oligomers via solid-phase synthesis techniques. The Fmoc protection group allows for efficient, orthogonal deprotection cycles, while the Bhoc group safeguards the cytosine nucleobase against side reactions. This monomer is particularly valuable for researchers constructing custom PNA sequences, enabling the design of probes, antisense molecules, or molecular beacons with tailored hybridization properties. Its chemical stability and compatibility with established synthesis workflows facilitate the reliable production of high-fidelity PNA constructs for a range of experimental needs.
Molecular recognition studies: Incorporation of this cytosine-containing PNA monomer enables the exploration of sequence-specific binding interactions between PNAs and complementary DNA or RNA targets. The neutral backbone of PNAs reduces electrostatic repulsion, resulting in stronger and more specific hybridization compared to traditional oligonucleotides. Researchers utilize oligomers synthesized from Fmoc-PNA-C(Bhoc)-OH to investigate hybridization kinetics, mismatch discrimination, and the thermodynamics of nucleic acid recognition, providing insights into the fundamental principles governing molecular recognition and nucleic acid structure.
Diagnostic probe development: Fmoc-protected PNA monomers bearing protected nucleobases are instrumental in the design and synthesis of PNA-based probes for molecular diagnostics. Oligomers constructed using this cytosine monomer exhibit exceptional sequence specificity and resistance to enzymatic degradation, making them suitable for the detection of single nucleotide polymorphisms, pathogenic sequences, or genetic mutations in biological samples. The robustness and versatility of PNA probes synthesized from such monomers support their integration into advanced diagnostic platforms, including fluorescence in situ hybridization (FISH) and microarray technologies.
Antisense and gene regulation research: PNAs assembled with Fmoc-PNA-C(Bhoc)-OH are widely used as sequence-specific antisense agents in gene expression studies. The strong binding affinity and resistance to nucleases allow these synthetic oligomers to effectively block transcription or translation by sterically hindering target nucleic acid sequences. Researchers leverage these properties to dissect gene function, elucidate regulatory mechanisms, and develop novel tools for the modulation of gene expression in vitro, providing a versatile platform for functional genomics studies.
Bioconjugation and functionalization: The presence of orthogonal protecting groups in Fmoc-PNA-C(Bhoc)-OH facilitates site-specific modifications and conjugation strategies. Following deprotection, the reactive termini of the synthesized PNA can be functionalized with a variety of reporter molecules, affinity tags, or other chemical entities. This capability enables the creation of multifunctional PNA constructs for applications such as biosensor development, surface immobilization, or targeted delivery systems, expanding the utility of PNA technology in both basic research and applied biotechnology.
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