Long-range stereo-relay: Relative and absolute configuration of 1,n-glycols from circular dichroism of liposomal porphyrin esters

Journal of the American Chemical Society

Volumn 126, Issue 32, 2004, Pages 9944-9945

  MacMillan, John B ^a   Molinski, Tadeusz F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; GLYCOL; LIPOSOME; PORPHYRIN DERIVATIVE;

ARTICLE; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; LIPID BILAYER; STEREOCHEMISTRY; TRANSMISSION ELECTRON MICROSCOPY;

CIRCULAR DICHROISM; ESTERS; GLYCOLS; LIPOSOMES; MOLECULAR CONFORMATION; PORPHYRINS; STEREOISOMERISM;

EID: 4043077679     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047741a     Document Type: Article

References (24)

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13. t 14.3 min) (See Supporting Information).
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18. 2O (2 mL) was added and the flask sonicated (∼60 s). The crude liposome preparation was twice heated (60 °C) and cooled to room temperature, then repeatedly extruded (×21) through a 100-nm membrane filter secured between two gastight 0.5-mL syringes (Liposofast, Avestin, Canada) to give unilamellar liposomes (see Figure 3).
19. max of TPP excitation (λ 418 nm) greatly reduce loss of CD signal from non-Rayleigh light scattering. CD of 1,5-glycol TPP esters in micelles (aq. 1-O-octyl glycoside) or 2D-liquid crystals gave inferior results.
20. We cannot exclude secondary effects, e.g. π-π stacking of porphyrin rings.
21. 3, MeOH). (>99% de by Mosher's analysis) (see Supporting Information).
22. CD (6c): λ 426 nm (Δε +36), 415 (-15). CD (7c): 426 (Δε +20), 415 (-7).
23. Fernández, F.; Garciá-Mera, X.; Rodríquez-Borges, J. E. Tetrahedron: Asymmetry 2001, 12, 365-386.
24. Bis-TPP esters of rigid dimeric sterol diol scaffolds have been shown to exhibit comparable ECCD at separations of ∼18 Å.