Boc PNA Monomers
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Boc PNA Monomers

CAS 149376-69-2
Catalog BAT-014352
Molecular Weight 527.54
Molecular Formula C24H29N7O7
Boc-PNA-A(Z)-OH
CAS 144564-94-3
Catalog BAT-014353
Molecular Weight 503.51
Molecular Formula C23H29N5O8
Boc-PNA-C(Z)-OH
CAS 169287-77-8
Catalog BAT-014354
Molecular Weight 543.54
Molecular Formula C24H29N7O8
Boc-PNA-G(Z)-OH
CAS 139166-80-6
Catalog BAT-014355
Molecular Weight 384.39
Molecular Formula C16H24N4O7
Boc-PNA-T-OH
CAS 149500-74-3
Catalog BAT-014356
Molecular Weight 370.36
Molecular Formula C15H22N4O7
Boc-PNA-U-OH
CAS 163081-03-6
Catalog BAT-014359
Molecular Weight 503.51
Molecular Formula C23H29N5O8
Boc-PNA-J(Z)-OH
Catalog BAT-014358
Molecular Weight 486.53
Molecular Formula C24H30N4O7
Boc-PNA-M(Z)-OH
Catalog BAT-014360
Molecular Weight 944.96
Molecular Formula C48H48N8O13
Boc-PNA-D(tetraZ)-OH
CAS 253438-99-2
Catalog BAT-014357
Molecular Weight 506.57
Molecular Formula C23H30N4O7S
Boc-PNA-thioU(PMB)-OH

BOC Sciences offers an extensive and high-quality range of Boc PNA Monomers and has a quality control system in place to analyze Boc PNA Monomers by MS, NMR, and HPLC to validate their structure and purity. We work with our customers to understand their needs and provide customized Boc PNA monomer synthesis services. PNA of different lengths, sequences and modifications are also available by using our Boc PNA monomers according to customer requirements.

Synthesis of Boc-protected PNA monomers.Fig.1 Synthesis of Boc-protected PNA monomers. (Amant et al., 2012)

What is Boc PNA monomer?

Boc PNA monomer is a protected chemical monomer used in the construction of peptide nucleic acid (PNA), an artificial nucleic acid molecule with high specificity and affinity, whose backbone consists of N-(2-aminoethyl)formamide monomers. Boc (tert-butyloxycarbonyl) is a commonly used protecting group for the protection of amino groups in chemical reactions.

The introduction of Boc PNA monomers has made PNA synthesis more flexible and versatile. By introducing Boc protecting groups at specific positions in the PNA sequence, the synthesis and modification process of PNA can be controlled to obtain the desired sequence and function. In addition, the introduction of Boc protecting groups can increase the solubility and stability of PNA and improve its performance in biological applications.

Classification of Boc PNA Monomers

Boc PNA monomers are mainly classified according to the base composition and are mainly divided into the following categories.

  • A (adenine) Class Monomers

A (Adenine) monomers contain adenine bases and are used to form base pairs with thymine (T) or uracil (U). For example, Boc-PNA-A(Z)-OH.

  • T (thymine)-like Monomers

T (thymine)-like monomers contain thymine bases and are used to form base pairs with adenine (A). For example, Boc-PNA-T-OH.

  • G (Guanine) Monomers

G (guanine) monomers contain guanine bases and are used to form base pairs with cytosine (C). For example, Boc-PNA-G(Z)-OH.

  • C (cytosine) Monomers

C (cytosine) monomers contain cytosine bases and are used to form base pairs with guanine (G). For example, Boc-PNA-C(Z)-OH.

Why are PNA Monomers Protected with Boc?

Boc in Boc-PNA monomers is mainly used to protect the amino (-NH2) functional group, which is protected for several reasons.

  • To Prevent Non-specific Reactions

Amino groups can easily react non-specifically with other reactants in chemical synthesis, leading to the occurrence of side reactions. By introducing a protecting group, the amino group can be prevented from participating in non-specific reactions, thus protecting the integrity of the target compound.

  • Selective Control of Reactions

The introduction of a protecting group can make a specific site in the synthesis process selective for a particular reaction. This is important for the protection and deprotection of specific functional groups during multi-step synthesis to ensure that the desired chemical transformation takes place at a specific site.

Advantages of Boc PNA Monomers

  • High-stability

Boc PNA monomer is highly chemically stable and resistant to enzymatic degradation and chemical changes in the environment. This gives Boc-PNA long-lasting biological activity in in vitro and in vivo applications.

  • High-affinity and specificity

Boc PNA monomer shows high affinity and specific binding capacity due to PNA's base pairing ability similar to DNA and RNA.

  • High-permeability

Since Boc PNA monomer is uncharged, it can more easily cross cell membranes and tissue barriers relative to charged DNA or RNA, achieving higher cell permeability.

  • High-selectivity

Boc PNA monomer shows high selectivity in hybridization with DNA and RNA, being able to distinguish even single base differences.

  • Resistance to Enzymatic Degradation

Due to its unnatural chemical structure, Boc PNA monomer shows high resistance to many nucleases, which increases stability and activity in organisms.

Reference:

  1. Amant A H S, et al. Synthesis and oligomerization of Fmoc/Boc-protected PNA monomers of 2, 6-diaminopurine, 2-aminopurine and thymine[J]. Organic & Biomolecular Chemistry, 2012, 10(4): 876-881.
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