Semipermeable lipid bilayers exhibit diastereoselectivity favoring ribose

Sacerdote and Szostak. 10.1073/pnas.0408440102.

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Supporting Text
Supporting Table 2
Supporting Table 3
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Supporting Figure 4

Fig. 4. Effect of solute concentration on the permeability of oleate membranes to water. Increasing the external solute concentration increased Pf in a solute-independent manner.

 

Table 2. RP-HPLC retention times and –ClogP values correlate poorly

 

Retention time, min*

-ClogP†

Solute

 

 

Erythritol

3.821

1.7076

dl-Threitol

3.869

1.7076

Adonitol

3.76

1.8768

Arabitol

3.741

1.8768

Xylitol

3.742

1.8768

Dulcitol

3.62

2.0460

Mannitol

3.693

2.0460

Sorbitol

3.692

2.0460

Arabinose

3.88

2.1759

Lyxose

3.772

2.1788

Ribopyranoses

3.941

2.1815

Ribose

 

2.1578

α-Xylopyranose

3.948

2.1812

β-Xylopyranose

3.689

2.1812

Xylose

 

2.2012

Ribulose

4.163

2.1345

Galactose

3.615

2.2527

Glucose

3.657

2.2159

Mannose

5.558

2.2193

Fructose

3.794

2.1607

l-Sorbose

3.688

2.1711

aRP-HPLC conditions: Alltima C18 column with pure water (0.75 ml/min) as the eluent.

bClogP values weighted for the proportions of acyclic, furanose, and pyranose forms present in sugar solutions at equilibrium (1-7).

1. Serianni, A. S., Clark, E. L. & Barker, R. (1979) Carbohydr. Res. 72, 79.

2. Serianni, A. S., Pierce, J., Huang, S. G. & Barker, R. (1982) J. Am. Chem. Soc. 104, 4037-4044.

3. Dworkin, J. P. & Miller, S. L. (2000) Carbohydr. Res. 329, 359-365.

4. Pigman, W. & Horton, D. (1972) in The Carbohydrates: Chemistry and Biochemistry (Academic, New York), 2nd Ed., Vol. IA, pp. 165-175.

5. Zhu, Y., Zajicek, J. & Serianni, A. S. (2001) J. Org. Chem. 66, 6244-6251.

6. Que, L., Jr., & Gray, G. R. (1974) Biochemistry 13, 146-153.

7. Wu, S., Serianni, A. S. & Vuorinen, T. (1990) Carbohydr. Res. 206, 1-12.





 

Table 3. Permeabilities coefficients for water (Pf) across fatty acid and phospholipid membranes

 

Membrane composition

 

Myristoleate*

Palmitoleate*

Oleate*

Oleate†

POPC*

DPPC/C/PA*

Solute

 

 

 

 

 

 

Erythritol

1.7

1.1

0.86

 

0.70

0.027

DL-threitol

1.8

1.1

0.86

 

0.72

0.027

Adonitol

1.7

1.1

0.86

 

 

 

Arabitol

1.7

1.1

0.81

 

 

 

Xylitol

1.7

1.1

0.83

 

 

0.026

Mannitol

1.8

0.90

0.81

0.72

 

0.027

Sorbitol

1.8

0.89

0.84

0.78

 

0.031

Arabinose

1.7

1.0

0.80

0.78

0.70

0.026

Lyxose

1.7

1.0

0.94

0.79

0.70

0.027

Ribose

1.7

1.0

0.78

0.75

0.69

0.026

D-xylose

1.7

1.1

0.83

0.76

0.71

0.026

L-xylose

1.8

1.0

0.86

 

0.71

0.027

Ribulose

 

 

0.97

 

 

 

Galactose

1.7

0.90

0.82

 

 

0.026

Glucose

1.7

0.90

0.85

0.74

 

 

Mannose

1.7

0.92

0.82

0.76

 

 

Fructose

1.7

1.1

0.85

0.73

 

 

L-Sorbose

1.8

1.0

0.81

0.81

 

 

Values reported in 10-2 cm/s. Chiral solutes are D-enantiomers unless otherwise noted.

*Experiments performed at 23° C with 1 ´ buffer, 0.5 M solute.

†Conditions as above but with 0.1 M solute. Literature values for phosphatidylcholine and egg lecithin membranes are 3-5 ´ 10-3 cm/s (1, 2).

1. Walter, A. & Gutknecht, J. (1986) J. Membr. Biol. 90, 207-217.

2. Boroske, E., Elwenspoek, M. & Helfrich, W. (1981) Biophys. J. 35, 95-109.

This Article

  1. Published online before print April 14, 2005, doi: 10.1073/pnas.0408440102 PNAS April 26, 2005 vol. 102 no. 17 6004-6008
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