Brezesinski, G.

Dobner, B.

Drescher, S.

Hause, G.

Janich, C.

Langner, A.

Meister, A.

Pawlowska, D.

Wölk, C.

ChemPhysChem

English

MPG.PuRe

Supporting InformationLamellar versus Micellar Structures—AggregationBehavior of a Three-Chain Cationic Lipid Designed forNonviral Polynucleotide TransferChristian Wçlk,*[a] Christopher Janich,[a] Dorota Pawlowska,[b] Simon Drescher,[a]Annette Meister,[c] Gerd Hause,[d] Bodo Dobner,[a] Andreas Langner,[a] andGerald Brezesinski[b]cphc_201500188_sm_miscellaneous_information.pdfAnalytical Data of DiTT4 and Precursors:  Precursor B (ditetradecylmalonic acid monoethyl ester): C33H64O4; M = 524.9 g mol-1; white crystals; yield: 54 %; melting point 33-35 °C; ESI-MS: 1047.6 [2M-H]-; elemental analysis: calc. C 75.52 H 12.29, found C 75.56 H 12.04; 1H-NMR [CDCl3, 400 MHz, 27 °C] δ[ppm]= 0.88 [t, 3J(H,H) = 7.0 Hz, 3H; -(CH2)2CH3]; 1.25-1.36 [m, 27H; -CH2-alkyl, -OCH2CH3]; 1.87-1.98 [m, 2H; (-CH2)CH(COEt)COOH]; 3.37 [t, 3J(H,H) = 7.3 Hz, 1H; (-CH2)CH(COEt)COOH]; 4.23 [q, 3J(H,H) = 7.1 Hz, 2H; -OCH2CH3] Precursor B (2-[(N-{6-[(tert.-butoxycarbonyl)amino]-1-oxo-1-[(N-tetradecyl)amino]hexan-(2S)-2-yl}amino)carbonyl]-2-tetradecylhexadecan acid): C56H109N3O6, M = 920.48 g mol-1; white waxy solid; yield: 92 %; melting point: 47-52 °C; ESI-MS: 919,6 [M-H]-; elemental analysis: calc. C 71.67 H 11.92 N 4.48 (C56H109N3O6+1×H2O), found C 72.00 H 11.78 N 4.68, 1H-NMR [CDCl3, 500 MHz, 27 °C] δ[ppm]= 0.88 [t, 3J(H,H) = 6.9 Hz, 9H; 3×-(CH2)2CH3]; 1.13-2.03 [m, 91H; -CH2-alkyl,  -(CH2)3CH2NHBOC, -OC(CH3)3]; 3.04-3.24 [m, 4H; -CH2NHBOC, -CH2NHCO-]; 4.38-4.40 [m, 1H; -COCH(NHCO-)CH2-]; 4.65 [s, 1H; -NHBOC]; 6.27 [s, 1H; -NHCO-]; 7.48 [s, 1H; -NHCO-]  DiTT4 (N-[6-amino-1-oxo-1-(N-tetradecylamino)hexan-(2S)-2-yl]-N`-{2-[N,N-bis(2-aminoethyl)amino]ethyl}-2,2-ditetradecylpropandiamide): C57H117N7O3; M: 948,58 g mol-1; colorless waxy solid; yield: 80 %; ESI-MS: 948,9 [M+H]+; HRMS: calc. 948.9291 Da (C57H118N7O3 [M+H]+) found 948.9323 Da; 1H-NMR: [CDCl3, 500 MHz, 27 °C] δ[ppm]= 0.87 [t, 3J(H,H) = 6.9 Hz, 9H; 3×-CH3]; 1.13-1.94 [m, 82H; -CH2-alkyl, -(CH2)3CH2NH2]; 2.57-2.65 [m, 6H; -CH2N(CH2CH2NH2)2]; 2.72-2.80 [m, 2H; lysin-CH2NH2]; 2.85 [t, 3J(H,H) = 5.1 Hz, 4H; 2×-CH2NH2]; 3.12-3.39 [m, 4H; 2×-CH2NHCO-]; 4.58-4.62 [m, 1H; -COCH(NHCO-)CH2-]; 7.63 [t, 3J(H,H) = 5.2 Hz, 1H; -NHCO-]; 7.37 [d, 3J(H,H) = 7.5 Hz, 1H; -COCH(NHCO-)CH2-]; 8.46 [t, 3J(H,H) = 4.4 Hz, 1H; -NHCO-]; 13C-NMR [CDCl3, 125 MHz, 27 °C] δ[ppm]= 14.1, 22.7, 24.98, 25.04, 27.0, 29.3, 29.48, 29.51, 29.52, 29.64, 29.65, 29.7, 29.89, 29.90, 30.8, 31.9, 32.3, 36.6, 37.3, 37.4, 39.1, 39.6, 40.8, 52.6, 53.9, 55.0, 57.3, 171.4, 172.5, 174.5 

Lamellar versus micellar structures-aggregation behavior of a three-chain cationic lipid designed for nonviral polynucleotide transfer

Christian Wölk

Christopher Janich

Dorota Pawlowska

Simon Drescher

Annette Meister

Gerd Hause

Bodo Dobner

Andreas Langner

Gerald Brezesinski

Crossref

Lamellar versus Micellar Structures-Aggregation Behavior of a Three-Chain Cationic Lipid Designed for Nonviral Polynucleotide Transfer

Lamellar versus micellar structures-aggregation behavior of a three-chain cationic lipid designed for nonviral polynucleotide transfer

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MPG.PuRe

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