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Boc PNA Monomers

Boc PNA Monomers

Creative Peptides provides a full range of peptide nucleic acid (PNA) products and related services. Click here to learn about PNA monomers prepared by Boc for the synthesis of PNA oligomers.

Browse our catalog below to find your products of interest.

Cat Product Name Description Size Price
BM-001Boc-PNA-C(Z)-OHPNA monomer incorporating a C nucleobase analogue through the Boc protecting group1 g/10 g/25 g/>25 g
BM-002Boc-A(Z)-Aeg-OHPNA monomer incorporating a A nucleobase analogue through the Boc protecting group1 g/5 g/10 g/25 g
BM-004Boc-DAP(Z)-Aeg-OH
BM-005Boc-G(Z)-Aeg-OHPNA monomer incorporating a G nucleobase analogue through the Boc protecting group1 g/5 g/10 g/25 g
BM-006Boc-J(Z)-Aeg-OH
BM-007Boc-T-Aeg-OHPNA monomer incorporating a T nucleobase analogue through the Boc protecting group1 g/5 g/10 g/25 g
BM-008Boc-PNA-ThioU(PMB)-Aeg-OH
BM-009Boc-PNA-D(tetraZ)-OH1 g/10 g/25 g/>25 g
BM-010Boc-PNA-M(Z)-OH1 g/5 g
BM-011Boc-PNA-thioU(PMB)-OH1 g/10 g/25 g/>25 g
BM-012Boc-PNA-U-OH1 g/5 g

Introduction

In 1950 and 1960, Merrifield proposed the principle of solid-phase chemical synthesis. At first, Merrifield used benzyloxycarbonyl to protect the alpha-amino group. However, it can induce side reactions. The Boc (t-Butyloxy carbonyl) protecting group was initially used mainly for the protection of amino groups in liquid phase peptide synthesis chemistry. Boc was subsequently developed to increase the yield of deprotection under mild conditions and to form a gas or low boiling point product. Because Boc deprotection can be almost quantified, Boc groups were soon used in solid-phase synthesis methods. Boc groups are widely used in combination with different strategies, such as unstable strategies (e.g. Boc/Z) and orthogonal strategies (e.g. Boc/Fmoc).

PNA was discovered in 1991, and the first T10 oligomers reported were composed of Boc-protected monomers. Thereafter, when A, C and G were prepared, the Z-group was used to protect the extra-ring amino group. Synthesis of PNA based on Boc/Z protection depends on the different acid-labile properties between these two groups.

Fig. 1 Structures of Boc/Z-protected PNA monomers (T. C. A and G).Fig. 1 Structures of Boc/Z-protected PNA monomers (T. C. A and G).

Advantages of Boc groups

  • Boc is stable to base hydrolysis and many nucleophilic reagents.
  • Boc is stable and more sensitive to catalytic hydrogenolysis.
  • The products produced during acid digestion do not bring about side reactions.
  • Most Boc amino acids can be crystallized.

References

  • de la Torre BG; et al. Synthesis of labelled PNA oligomers by a post-synthetic modification approach. Bioorg Med Chem Lett. 2003 Feb 10; 13(3): 391-3.
  • Manicardi A; et al. PNA bearing 5-azidomethyluracil: a novel approach for solid and solution phase modification. Artif DNA PNA XNA. 2012 Apr-Jun; 3(2): 53-62.

For Research Use Only. Not For Clinical Use.