42267-27-6

Basic information

• Product Name: N-[4-[(4S)-2,5-dioxooxazolidin-4-yl]butyl]-2,2,2-trifluoro-acetamide
• Synonyms: N-[4-[(4S)-2,5-dioxooxazolidin-4-yl]butyl]-2,2,2-trifluoro-acetamide;e-Trifluoroacetyl-Lysine, NCA;N-Trifluoroacetyl-L-lysine N-carboxyanhydride;N-(4-(2,5-Dioxo-4-oxazolidinyl)butyl)-2,2,2-trifluoroacetamide;N6-Trifluoroacetyl-L-lysine N-Carboxyanhydride;(S)-N-[4-(2,5-Dioxo-4-oxazolidinyl)butyl]-2,2,2-trifluoroacetaMide;N-[4-[(4S)-2,5-Dioxo-4-oxazolidinyl]butyl]-2,2,2-trifluoroacetaMide;AcetaMide,N-[4-[(4S)-2,5-dioxo-4-oxazolidinyl]butyl]-2,2,2-trifluoro-
• CAS NO: 42267-27-6
• Molecular Formula: C₉H₁₁F₃N₂O₄
• Molecular Weight: 268.19
• EINECS: 1592732-453-0
• Product Categories: AMINOACIDS DERIVATIVES;Amino Acids & Derivatives;Aromatics;Chiral Reagents;Heterocycles
• Mol File: 42267-27-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 92-93℃ (DEC.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.377
• Refractive Index: 1.436
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 9.27±0.40(Predicted)
• CAS DataBase Reference: N-[4-[(4S)-2,5-dioxooxazolidin-4-yl]butyl]-2,2,2-trifluoro-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-[(4S)-2,5-dioxooxazolidin-4-yl]butyl]-2,2,2-trifluoro-acetamide(42267-27-6)
• EPA Substance Registry System: N-[4-[(4S)-2,5-dioxooxazolidin-4-yl]butyl]-2,2,2-trifluoro-acetamide(42267-27-6)

Safety Data

• Hazardous Substances Data: 42267-27-6(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Solid

Uses

Different sources of media describe the Uses of 42267-27-6 differently. You can refer to the following data:
1. Used in the synthesis of new arborescent architectures of poly(L-lysine), called lysine dendrigraft (DGL) polymers. ?DGL polymers were prepd. through a multiple-generation scheme (up to generation 5) in a weakly acidic aq. medium by polycondensing N.vepsiln.-trifluoroacetyl-L-lysine-N-carboxyanhydride (Lys(Tfa)-NCA) onto the previous generation G(n-1) of DGL, which was used as a macroinitiator.
2. L-Lys(Tfa)-NCA can be used in the synthesis of new arborescent architectures of poly(L-lysine), called lysine dendrigraft (DGL) polymers.

InChI:InChI=1/C9H11F3N2O4/c10-9(11,12)7(16)13-4-2-1-3-5-6(15)18-8(17)14-5/h5H,1-4H2,(H,13,16)(H,14,17)/t5-/m0/s1

Upstream product

• 10009-20-8 (S)-6-trifluoroacetylamino-2-aminohexanoic acid 
• 503-38-8 trichloromethyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 75-44-5 phosgene 
• 112139-31-8 C₉H₁₂ClF₃N₂O₄ 

Downstream Products

• 58191-22-3 {(S)-1-[(S)-1-(2-Methoxy-ethylcarbamoyl)-5-(2,2,2-trifluoro-acetylamino)-pentylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester 
• 58191-21-2 {(S)-1-[(S)-1-Butylcarbamoyl-5-(2,2,2-trifluoro-acetylamino)-pentylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester 
• 58191-25-6 (S)-2-[(S)-2-(2-Chloro-acetylamino)-3-phenyl-propionylamino]-6-(2,2,2-trifluoro-acetylamino)-hexanoic acid butylamide 
• 58191-24-5 (S)-2-((S)-2-Amino-3-phenyl-propionylamino)-6-(2,2,2-trifluoro-acetylamino)-hexanoic acid (2-methoxy-ethyl)-amide 
• 58191-23-4 (S)-2-((S)-2-Amino-3-phenyl-propionylamino)-6-(2,2,2-trifluoro-acetylamino)-hexanoic acid butylamide 
• 103300-89-6 N^ε-(trifluoroacetyl)-L-lysyl-L-proline 

Relevant articles and documents

An expeditious multigram-scale synthesis of lysine dendrigraft (DGL) polymers by aqueous n-carboxyanhydride polycondensation

The synthesis and characterisation of new arborescent architectures of poly(L-lysine), called lysine dendrigraft (DGL) polymers, are described. DGL polymers were prepared through a multiple-generation scheme (up to generation 5) in a weakly acidic aqueous medium by polycondensing Nε- trifluoroacetyl-L-lysine-N-carboxyanhydride (Lys(Tfa)-NCA) onto the previous generation G(n-1) of DGL, which was used as a macroinitiator. The first generation employed spontaneous NCA polycondensation in water without a macroinitiator; this afforded lowmolecular-weight, linear poly(L-lysine) G1 with a polymerisation degree of 8 and a polydispersity index of 1.2. The spontaneous precipitation of the growing Nε-Tfa-protected polymer (GnP) ensures moderate control of the molecular weight (with unimodal distribution) and easy work-up. The subsequent alkaline removal of Tfa protecting groups afforded generation Gn of DGL as a free form (with 35-60% overall yield from NCA precursor, depending on the DGL generation) that was either used directly in the synthesis of the next generation (G(n+1)) or collected for other uses. Unprotected forms of DGL G1-G5 were characterised by size-exclusion chromatography, capillary electrophoresis and 1H NMR spectroscopy. The latter technique allowed us to assess the branching density of DGL, the degree of which (ca. 25%) turned out to be intermediate between previously described dendritic graft poly(L-lysines) and lysine dendrimers. An optimised monomer (NCA) versus macroinitiator (DGL G(n-1)) ratio allowed us to obtain unimodal molecular weight distributions with polydispersity indexes ranging from 1.3 to 1.5. Together with the possibility of reaching high molecular weights (with a polymerisation degree of ca. 1000 for G5) within a few synthetic steps, this synthetic route to DGL provides an easy, cost-efficient, multigram-scale access to dendritic polylysines with various potential applications in biology and in other domains.

METHOD FOR PREPARATION OF N-CARBOXYANHYDRIDES

The invention discloses a method for the preparation off N-carboxyanhydrides (NCAs) by reaction of amino acids with phosgene.(II)

Directed interactions of block copolypept(o) ides with mannose-binding receptors: Peptomicelles targeted to cells of the innate immune system

Core-shell structures based on polypept(o)ides combine stealth-like properties of the corona material polysarcosine with adjustable functionalities of the polypeptidic core. Mannose-bearing block copolypept(o)ides (PSar-block-PGlu(OBn)) have been synthesized using 11-amino-3,6,9-trioxa-undecyl-2,3,4,6-tetra-O-acetyl-O-α-D-mannopyranoside as initiator in the sequential ring-opening polymerization of α-amino acid N-carboxyanhydrides. These amphiphilic block copolypept(o)ides self-assemble into multivalent PeptoMicelles and bind to mannose-binding receptors as expressed by dendritic cells. Mannosylated micelles showed enhanced cell uptake in DC 2.4 cells and in bone marrow-derived dendritic cells (BMDCs) and therefore appear to be a suitable platform for immune modulation.