852527-45-8

Basic information

• Product Name: N-Succinimidyl 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoate
• Synonyms: 2,5-Pyrrolidinedione, 1-[(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-1-oxoundecyl)oxy]-;4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluor-undecansure-N-succinimidylester;N-Succinimidyl 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoate >=95%;N-Succinimidyl 3-(perfluorooctyl)propionate;N-Succinimidyl 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoate;N-Succinimidyl 3-(perfluorooctyl)propionate, N-Succinimidyl 2H,2H,3H,3H-perfluoroundecanoate
• CAS NO: 852527-45-8
• Molecular Formula: C15H8F17NO4
• Molecular Weight: 589.2011744
• Mol File: 852527-45-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 140-146°C
• Boiling Point: 330.5°C at 760 mmHg
• Flash Point: 153.7°C
• Appearance: /
• Density: 1.658g/cm³
• Vapor Pressure: 0.000166mmHg at 25°C
• Refractive Index: 1.356
• Storage Temp.: ?20°C
• CAS DataBase Reference: N-Succinimidyl 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoate(CAS DataBase Reference)
• NIST Chemistry Reference: N-Succinimidyl 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoate(852527-45-8)
• EPA Substance Registry System: N-Succinimidyl 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoate(852527-45-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 852527-45-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H8F17NO3/c16-8(17,4-3-7(36)33-5(34)1-2-6(33)35)9(18,19)10(20,21)11(22,23)12(24,25)13(26,27)14(28,29)15(30,31)32/h1-4H2

Upstream product

• 34598-33-9 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoic acid 
• 105832-38-0 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 

Relevant articles and documents

Perfluoroalkyl chains direct novel self-assembly of insulin

The self-assembly of biopharmaceutical peptides into multimeric, nanoscale objects, as well as their disassembly to monomers, is central for their mode of action. Here, we describe a bioorthogonal strategy, using a non-native recognition principle, for control of protein self-assembly based on intermolecular fluorous interactions and demonstrate it for the small protein insulin. Perfluorinated alkyl chains of varying length were attached to desB30 human insulin by acylation of the ε-amine of the side-chain of LysB29. The insulin analogues were formulated with ZnII and phenol to form hexamers. The self-segregation of fluorous groups directed the insulin hexamers to self-assemble. The structures of the systems were investigated by circular dichroism (CD) spectroscopy and synchrotron small-angle X-ray scattering. Also, the binding affinity to the insulin receptor was measured. Interestingly, varying the length of the perfluoroalkyl chain provided three different scenarios for self-assembly; the short chains hardly affected the native hexameric structure, the medium-length chains induced fractal-like structures with the insulin hexamer as the fundamental building block, while the longest chains lead to the formation of structures with local cylindrical geometry. This hierarchical self-assembly system, which combines ZnII mediated hexamer formation with fluorous interactions, is a promising tool to control the formation of high molecular weight complexes of insulin and potentially other proteins.