N-trifluoroacyl lysine derivatives in the synthesis of L-Lysyl-L-glutamic acid

Cherevin, M. S.; Gulevich, T. G.; Popova, L. A.; Зубрейчук, З. П.; Knizhnikov, V. A.

doi:10.1134/s1070428007100028

Cited by 5 publications

(3 citation statements)

References 10 publications

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“…49,50 Melting points (Glu(OBzl)NCA: mp = 93.7 °C, Lys (TFA): mp = 101 °C, SarNCA: mp = 104.3 °C) were in good agreement with the literature or even higher than those reported which accounts for high purity. [51][52][53] All the synthesized NCAs were stored at −80 °C under a nitrogen atmosphere over several months without any detectable degradation or oligomerization.…”

Section: Polymer Synthesis and Functionalizationmentioning

confidence: 99%

Evaluating chemical ligation techniques for the synthesis of block copolypeptides, polypeptoids and block copolypept(o)ides: a comparative study

et al. 2015

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Section: Polymer Synthesis and Functionalizationmentioning

confidence: 99%

Evaluating chemical ligation techniques for the synthesis of block copolypeptides, polypeptoids and block copolypept(o)ides: a comparative study

et al. 2015

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“…The crude product was recrystallized twice with absolute THF/Hexane. 10.43 g of the purified product (39,0 mmol; 75% yield; colorless needles, melting point: 101 8C (lit: 92-93 8C) [54] )) were obtained and stored in a Schlenk tube at À80 8C. 1 …”

Section: 4mentioning

confidence: 99%

Introducing PeptoPlexes: Polylysine‐block‐Polysarcosine Based Polyplexes for Transfection of HEK 293T Cells

Heller

Birke

Huesmann

et al. 2014

Macromolecular Bioscience

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A series of well-defined polypeptide-polypeptoid block copolymers based on the body's own amino acids sarcosine and lysine are prepared by ring opening polymerization of N-carboxyanhydrides. Block lengths were varied between 200-300 for the shielding polysarcosine block and 20-70 for the complexing polylysine block. Dispersity indexes ranged from 1.05 to 1.18. Polylysine is polymerized with benzyloxycarbonyl as well as trifluoroacetyl protecting groups at the ϵ-amine group and optimized deprotection protocols for both groups are reported. The obtained block ionomers are used to complex pDNA resulting in the formation of polyplexes (PeptoPlexes). The PeptoPlexes can be successfully applied in the transfection of HEK 293T cells and are able to transfect up to 50% of cells in vitro (FACS assay), while causing no detectable toxicity in an Annexin V assay. These findings are a first indication that PeptoPlexes may be a suitable alternative to PEG based non-viral transfection systems.

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“…The crude product was recrystallized twice with absolute THF/hexane. 10.43 g of the purified product (39.0 mmol; 75% yield; colorless needles; melting point: 101 8C (lit: 92-93 8C) [53] ) were obtained and stored in a Schlenk tube at -80 8C.…”

Section: Tetraethylene Glycol Monotosylatementioning

confidence: 99%

Directed Interactions of Block Copolypept(o)ides with Mannose‐binding Receptors: PeptoMicelles Targeted to Cells of the Innate Immune System

Heller

Mohr

Birke

et al. 2015

Macromolecular Bioscience

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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.

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N-trifluoroacyl lysine derivatives in the synthesis of L-Lysyl-L-glutamic acid

Cited by 5 publications

References 10 publications

Evaluating chemical ligation techniques for the synthesis of block copolypeptides, polypeptoids and block copolypept(o)ides: a comparative study

Evaluating chemical ligation techniques for the synthesis of block copolypeptides, polypeptoids and block copolypept(o)ides: a comparative study

Introducing PeptoPlexes: Polylysine‐block‐Polysarcosine Based Polyplexes for Transfection of HEK 293T Cells

Directed Interactions of Block Copolypept(o)ides with Mannose‐binding Receptors: PeptoMicelles Targeted to Cells of the Innate Immune System

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