Spacer C18 CE Phosphoramidite

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Spacer C18 CE Phosphoramidite

Spacer C18 CE Phosphoramidite | 125607-09-2

Catalog Number R10-0006
Category DNA Stains
Molecular Formula C42H61N2O10P
Molecular Weight 784.91
Catalog Number Size Price Quantity
R10-0006 -- $--

Product Introduction

Hexaethylene glycol phosphoramidite is used to insert a spacer arm in an oligonucleotide and may be added in multiple additions when a longer spacer is required.

Chemical Information

Synonyms Spacer 18 Amidite; Hexaethylene glycol phosphoramidite; 18-O-(4,4'-Dimethoxytrityl)-hexaethylene glycol-1-[[(2-cyanoethyl)-(N,N-diisopropyl)]-Phosphoramidite; 1,1-bis(4-methoxyphenyl)-1-phenyl-2,5,8,11,14,17-hexaoxanonadecan-19-yl (2-cyanoethyl) diisopropylphosphoramidite; Spacer 18 Phosphoramidite; Phosphoramidous acid, N,N-bis(1-methylethyl)-, 19,19-bis(4-methoxyphenyl)-19-phenyl-3,6,9,12,15,18-hexaoxanonadec-1-yl 2-cyanoethyl ester; 19,19-Bis(4-methoxyphenyl)-19-phenyl-3,6,9,12,15,18-hexaoxanonadec-1-yl 2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite; Spacer Phosphoramidite 18; DMT Hexaethylene Glycol phosphoramidite
Purity ≥95.0%
IUPAC Name 3-[2-[2-[2-[2-[2-[2-[bis(4-methoxyphenyl)-phenylmethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
Canonical SMILES CC(C)N(C(C)C)P(OCCC#N)OCCOCCOCCOCCOCCOCCOC(C1=CC=CC=C1)(C2=CC=C(C=C2)OC)C3=CC=C(C=C3)OC
InChI InChI=1S/C42H61N2O10P/c1-35(2)44(36(3)4)55(53-22-10-21-43)54-34-32-51-30-28-49-26-24-47-23-25-48-27-29-50-31-33-52-42(37-11-8-7-9-12-37,38-13-17-40(45-5)18-14-38)39-15-19-41(46-6)20-16-39/h7-9,11-20,35-36H,10,22-34H2,1-6H3
InChI Key ZTCKUVQHKIMCLI-UHFFFAOYSA-N
Solubility good in most organic solvents
Appearance colorless/yellowish oil
Boiling Point 763.6±60.0°C (Predicted)
  • Product Specification
  • Application
Storage Store at -20°C

Hexaethylene glycol phosphoramidite is a chemical compound used primarily in the synthesis of modified oligonucleotides. It belongs to the family of glycol phosphoramidites which are utilized in the field of molecular biology for the preparation and modification of nucleic acids. The structure of hexaethylene glycol phosphoramidite includes six ethylene glycol units which provide flexibility and hydrophilicity, enhancing the solubility of the oligonucleotides in aqueous solutions. This compound is often employed in solid-phase synthesis due to its capacity to form stable phosphite triester intermediates, which are essential in the stepwise synthesis of DNA or RNA sequences.

One of the key applications of hexaethylene glycol phosphoramidite is in the synthesis of polyethylene glycol (PEG)-modified oligonucleotides. This modification is crucial for increasing the stability and biocompatibility of oligonucleotides, thereby enhancing their therapeutic potential. By attaching PEG chains to oligonucleotides, researchers can increase the molecules’ resistance to nucleases, improve their pharmacokinetics, and reduce immunogenic responses. In therapeutic contexts, this translates to more effective drug delivery systems, especially in treatments involving nucleic acid-based drugs.

Another significant application of hexaethylene glycol phosphoramidite is in the construction of DNA microarrays. These microarrays are important tools used in genomics for the study of gene expression and genetic variations across different biological samples. The phosphoramidite chemistry allows for the precise and rapid synthesis of numerous DNA sequences directly on a solid surface, facilitating high-throughput analysis. This technology significantly aids in diverse applications including disease diagnosis, personalized medicine, and the development of novel therapeutic strategies by allowing researchers to access comprehensive genomic information quickly and efficiently.

In addition, hexaethylene glycol phosphoramidite finds use in the development of aptamers. Aptamers are short, single-stranded DNA or RNA molecules that can bind to specific targets like proteins, small molecules, or even cells with high affinity. The incorporation of hexaethylene glycol units can enhance the binding properties and stabilize the aptamer structures, making them suitable for use in diagnostic assays, biosensors, and as therapeutic agents. Aptamers are particularly valued for their ability to be synthesized chemically, allowing modifications that can enhance their stability and specificity, thus broadening their application scope.

Lastly, hexaethylene glycol phosphoramidite is critical in the field of antisense oligonucleotide (ASO) technology. ASOs are designed to specifically bind to mRNA molecules, modulating gene expression by promoting degradation or altering splicing patterns. The use of hexaethylene glycol phosphoramidite in ASO synthesis provides enhanced aqueous solubility and reduced toxicity, making these molecules more viable for clinical applications. This application is particularly impactful in the development of treatments for genetic disorders, where precise manipulation of gene expression can lead to significant therapeutic benefits.

Computed Properties

XLogP3 5.3
Hydrogen Bond Donor Count 0
Hydrogen Bond Acceptor Count 12
Rotatable Bond Count 31
Exact Mass 784.40638314 g/mol
Monoisotopic Mass 784.40638314 g/mol
Topological Polar Surface Area 119Ų
Heavy Atom Count 55
Formal Charge 0
Complexity 949
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 1
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes

Patents

Publication NumberTitlePriority Date
US-10308943-B2 Compositions with improved intravitreal half-life and uses thereof 2016-02-08
US-2018127754-A1 Bivalent antisense oligonucleotides 2010-03-24
US-5674856-A Modified oligodeoxyribonucleoditides 1993-01-29
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