208402-69-1

Basic information

• Product Name: pentafluorophenyl oleate
• Synonyms: pentafluorophenyl oleate
• CAS NO: 208402-69-1
• Molecular Weight: 448.517
• Mol File: 208402-69-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: pentafluorophenyl oleate(CAS DataBase Reference)
• NIST Chemistry Reference: pentafluorophenyl oleate(208402-69-1)
• EPA Substance Registry System: pentafluorophenyl oleate(208402-69-1)

Safety Data

• Hazardous Substances Data: 208402-69-1(Hazardous Substances Data)

Upstream product

• 112-80-1 cis-Octadecenoic acid 
• 14533-84-7 pentafluorophenyl trifloroacetate 
• 771-61-9 2,3,4,5,6-pentafluorophenol 

Downstream Products

• 143-28-2 oleoyl alcohol 

Relevant articles and documents

Oligonucleotides Containing 1-Aminomethyl or 1-Mercaptomethyl-2-deoxy- d -ribofuranoses: Synthesis, Purification, Characterization, and Conjugation with Fluorophores and Lipids

Oligonucleotide conjugates are widely used as therapeutic drugs, gene analysis, and diagnostic tools. A critical step in the biologically relevant oligonucleotide conjugates is the design and synthesis of functional molecules that connect oligonucleotide with ligands. Here, we report the synthesis and application for oligonucleotide functionalization of novel tethers based on aminomethyl and mercaptomethyl sugar derivatives. Starting from a common cyano sugar precursor, three novel phosphoramidites have been prepared in the two α- and β-anomeric forms. The mercaptomethyl sugar was protected with the S-acetyl group, while two different protecting groups have been developed for the aminomethyl sugar. These two protecting groups are orthogonal, as they can be removed independently using photolysis or ammonolysis. This combination allowed the introduction of two different ligands in a single oligonucleotide.

Fatty acid conjugation enhances potency of antisense oligonucleotides in muscle

Enhancing the functional uptake of antisense oligonucleotide (ASO) in the muscle will be beneficial for developing ASO therapeutics targeting genes expressed in the muscle. We hypothesized that improving albumin binding will facilitate traversal of ASO from the blood compartment to the interstitium of the muscle tissues to enhance ASO functional uptake. We synthesized structurally diverse saturated and unsaturated fatty acid conjugated ASOs with a range of hydrophobicity. The binding affinity of ASO fatty acid conjugates to plasma proteins improved with fatty acid chain length and highest binding affinity was observed with ASO conjugates containing fatty acid chain length from 16 to 22 carbons. The degree of unsaturation or conformation of double bond appears to have no influence on protein binding or activity of ASO fatty acid conjugates. Activity of fatty acid ASO conjugates correlated with the affinity to albumin and the tightest albumin binder exhibited the highest activity improvement in muscle. Palmitic acid conjugation increases ASO plasma Cmax and improved delivery of ASO to interstitial space of mouse muscle. Conjugation of palmitic acid improved potency of DMPK, Cav3, CD36 and Malat-1 ASOs (3- to 7-fold) in mouse muscle. Our approach provides a foundation for developing more effective therapeutic ASOs for muscle disorders.

N-acylated cyclohexapeptide compounds

Compounds of the formula wherein R is a residue of a carboxylic acid are described. The compounds are antimicrobial agents.