Locked Nucleic Acid Phosphoramidites

We reintroduce the starting materials for Locked Nucleic Acid oligonucleotides in September this year as part of our Proligo Reagents product portfolio.

Our world-class expertise in nucleic acid synthesis reagents tracks back to 1986 when Dr. Hubert Koster first commercialized the synthesis of ß-cyanoethylphosphoramidites. Since then, we have refined and perfected the production of phosphoramidites. Today, we offer the highest quality phosphoramidites along with best in class technical expertise, customization and service.

Locked Nucleic Acid phosphoramidites are the key building blocks in the synthesis of Locked Nucleic Acid oligonucleotides. Locked Nucleic Acid is a nucleic acid analog imparting superior hybridization characteristics and enhanced biostability, compared to natural DNA and RNA.
What is Locked Nucleic Acid?

Locked Nucleic Acid is a type of nucleic acid analog that contains a 2′-0, 4′-C methylene bridge. This bridge restricts the flexibility of the ribofuranose ring and locks the structure into a rigid bicyclic formation, conferring enhanced hybridization performance and exceptional biostability.
Duplexes including Locked Nucleic Acid oligonucleotides are considerably more thermally stable than similar duplexes constituted from DNA or RNA oligonucleotides, conferring the following advantages:

  • Increased melting temperature of the oligonucleotide duplex - by 3 to 8 °C per incorporated Locked Nucleic Acid nucleoside in the oligomer
  • Dramatically enhanced affinity towards complementary DNA or RNA
  • Superior discrimination between matched and mismatched target nucleic acids
  • Hybridization to complementary nucleic acids, even under low salt conditions and in the presence of chaotropic agents
  • Increased stability of the oligonucleotide in biological fluids
  • Strand invasion capability
Locked Nucleic Acid oligonucleotides can be applied to almost all platforms that employ synthetic oligonucleotides:

  • Hybridization probes for the detection of nucleic acids and genotyping e.g. Molecular Beacons probes, Padlock probes, TaqMan® probes and probes for in situ hybridization
  • Capture probes for target enrichment, sample preparation and affinity chromatography
  • Target validation through antisense technology and siRNA
  • Oligonucleotides for therapeutic applications, such as antisense oligonucleotides, aptamers, siRNA, alternative splicing
Key Features of Locked Nucleic Acid Phosphoramidites

  • Locked Nucleic Acid oligonucleotides are prepared by phosphoramidite chemistry.
  • Standard DNA synthesizer platforms can be employed. No change is required in the reagents commonly used for DNA synthesis.
  • To further enhance the hybridization characteristics of Locked Nucleic Acid, 5-methyl-cytidine is employed instead of cytidine.
  • Locked Nucleic Acid monomers are as soluble in acetonitrile as their DNA counterparts (except for the 5-methyl-cytidine derivative, which requires the application of 10-20%, dichloromethane as a co-solvent)
  • Mixmer oligonucleotides containing Locked Nucleic Acid, DNA and/or RNA monomers can be assembled easily.
  • Locked Nucleic Acid oligonucleotides with predefined melting temperatures (Tm) can be designed and prepared.
Other Locked Nucleic Acid Considerations

  • Oligonucleotides containing Locked Nucleic Acid can also include modifications and non-radioactive labels, similar to DNA oligonucleotides.
  • Locked Nucleic Acid oligonucleotides can be phosphorothioated by standard procedures.
  • In most respects, Locked Nucleic Acid may be handled like DNA: it is soluble in aqueous buffers, can be ethanol precipitated, dried and resuspended, and can be analyzed by gel electrophoresis, HPLC and MALDITOF.
  • The synthesis of Locked Nucleic Acid oligonucleotides is similar to DNA oligonucleotide synthesis, but with an elongated coupling time of 8 minutes. Deprotection should be conducted with aqueous ammonia, since the C-derivative is protected with the conventional benzoyl protective group. Fast-deprotecting reagents, such as methylamine, should be avoided.
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DMT-locA(bz) Phosphoramidite

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AL11400   DMT-locA(bz) Phosphoramidite C48H52N7O8P    
AL11430   DMT-locA(bz) Phosphoramidite C48H52N7O8P configured for ABI
 
AL11480   DMT-locA(bz) Phosphoramidite C48H52N7O8P configured for PerkinElmer
 

DMT-locG(ib) Phosphoramidite

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GL11400   DMT-locG(ib) Phosphoramidite C45H54N7O9P    
GL11430   DMT-locG(ib) Phosphoramidite C45H54N7O9P configured for ABI
 
GL11480   DMT-locG(ib) Phosphoramidite C45H54N7O9P configured for PerkinElmer
 

DMT-locMeC(bz) Phosphoramidite

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CL11400   DMT-locMeC(bz) Phosphoramidite C48H54N5O9P    
CL11430   DMT-locMeC(bz) Phosphoramidite C48H54N5O9P configured for ABI
 
CL11480   DMT-locMeC(bz) Phosphoramidite C48H54N5O9P configured for PerkinElmer
 

DMT-locT Phosphoramidite

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TL11430   DMT-locT Phosphoramidite C41H49N4O9P configured for ABI
 
TL11480   DMT-locT Phosphoramidite C41H49N4O9P configured for PerkinElmer