Modification by Introducing Chiral Branches
The backbone of PNA is N-(aminoethyl) glycine. At present, many studies have introduced chiral branches at α, β, and γ to improve its shortcomings and make PNA better in the fields of biology, biotechnology, medicine, etc.
Creative Peptides provides comprehensive PNA modification services, including the introduction of chiral branched chains with different functions at different sites to meet customer requirements for PNA monomer functions.
The introduction of branched chains can make monomers become chiral molecules with little effect on hybridization properties. Several commonly used methods of introducing side chains include the improvement of classic monomer synthesis methods, the use of various natural amino acids to introduce branch chains, Ugi 4cc reaction and so on.
● Introduce a chiral branch at the α position
The introduction of amino acid residues at the α-position for modification is one of the methods for preparing chiral peptide nucleic acid monomers. At present, a variety of modified monomers and sequences have been synthesized.
Substituted amino acid
|Lys (D type and L type), Ser (D type and L type), D-Glu, L-Asp, L-IleVal, Leu, Phe, Glu, Asn, His, Thr, Arg, Tyr, Trp|
● Introduce a chiral branch at the β position
The β-position of the PNA backbone corresponds to the C4 on the deoxyribose moiety in DNA. C4 is a chiral C atom. Therefore, the introduction of a chiral center at the β-position may affect the binding ability of PNA and DNA.
● Introduce a chiral branch at the γ position
modified PNA monomers (He Y.X. et al. 2006)
Compared with the α-position, the modification of the γ-position is more conducive to improving the binding affinity of PNA and DNA. The suitable orthogonal protecting groups for PNA monomers with thiomethyl group introduced at the γ position are: Boc and PMB, the other protecting groups are Fmoc and StBu. The thiomethyl modified PNA monomer can be used as the extension of the PNA chain, and can also be used as the modified monomer of the binding site.
➢ The synthesis of PNA monomers with chiral amino acids as starting materials can make the introduction of functional groups more convenient.
➢ Help improve the physical and chemical properties of peptide nucleic acids, such as enhancing water solubility and improving membrane permeability.
➢ At the same time, this modification can also be used to simulate new functions.
Why Choose Us
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- He Y.X. et al.Research progress of monomer skeleton modification of peptide nucleic acids. Chinese journal of medicinal chemistry. 2006, 16(4):253-258.
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