Re: Peptide solubility

Igor Rodionov (rodionov@fibkh.serpukhov.su)
Wed, 2 Dec 1998 15:11:11 +0300

Dear Ulf,
I am not aware of any solubility predicting software, but I do know few
papers concerning this problem. The list of relevant references you will
find below. The first one is the most important.
For solubility prediction beta structure/sheet propensities of amino acids
(Chou-Fasman or the like) seems to be generally more useful than
hydrophobicity parameters.
Regars,
Igor

1. Narita, M., Ishikawa, K., Chen, J-Y., and Kim, Y. Prediction and
improvement of protected peptide solubility in organic solvents.- Int. J.
Peptide Protein Res., 1984, v.24, pp.580-587.

Narita, M., Honda, S., Umeyama, H., and Obana, S. The Solubility of
Peptide Intermediates in Organic Solvents. Solubilizing Potential of
Hexafluoro-2-propanol.- Bull. Chem. Soc. Jpn., 1988, v.61, pp.281-284.
Narita, M., Honda, S., and Obana, S. The -Sheet Structure-Disrupting
Potential of Electron-Donor and -Acceptor Solvents and Role of Mixed
Solvents in Solvation of Peptides.- Bull. Chem. Soc. Jpn., 1989, v.62, n.1,
pp.342-344.
Narita, M., Lee, J-S., Hayashi, S., Yamazaki, Y., and Hitomi, M. The
Solubility and Conformation of Protected Tri- to Heptapeptides in a Variety
of Organic Solvents and the Classification of Organic Solvents Based on
Their Solvating Potential for Protected Peptides.- Bull. Chem. Soc. Jpn.,
1993, v.66, n.2, pp.494-499.
Narita, M., Ogura, T., Sato, K., and Honda, S. Desing of the Synthetic
Route for Peptides and Proteins Based on the Solubility Prediction Method.
I. Synthesis and Solubility Properties of Human Proinsulin C-Peptide
Fragments.- Bull. Chem. Soc. Jpn., 1986, v.59, n.8, pp.2433-2438.
Narita, M., Umeyama, H., and Sasaki, C. Weak dependence of octapeptide
solubility in organic solvents on the amino acid sequence.- Int. J.
Peptide. Protein. Res., 1989, v.33, pp.340-344.
Narita, M., Doi, M., Nakai, T., and Takegahara, H. Synthesis and
solubility properties of peptide fragments of human hemoglobin -chain
(123-136).- Int. J. Peptide. Protein. Res., 1988, v.32, n. , pp.200-207.
Narita, M., Doi, M., Kudo, K., and Terauchi, Y. Conformations in the
Solid State and Solubility Properties of Protected Homooligopeptides of
Glycine and -Alanine.- Bull. Chem. Soc. Jpn., 1986, v.59, pp.3553-3557.
Mor , H., and Ichimura, K. Solubility and Coupling Reactivity of
Protected Peptides in Highly Polar Solvents.- Bull. Chem. Soc. Jpn., 1989,
v.62, n.8, pp.2730-2732.
Kuroda, H., Chen, Y-N., Kimora, T., and Sakakibara, S. Powerful solvent
systems useful for synthesis of sparingly-soluble peptides in solution.-
Im. J. Peptide Protein Res., 1992, v.40, n.3/4, pp.294-299.
Toniolo, C., Bonora, G.M., Mutter, M., and Maser, F. Self-association and
Solubility of Peptides. An Infrared Absorption Method for Quantitative
Titration of the Extent of Self-Association in Poly(ethylene glycol)-bound
Peptides.- J. Chem. Soc. Chem. Commun., 1983, pp.1298-1299.
Toniolo, C., Bonora, G.M., and Moretto, V. Self-Association and
Solubility of Peptides. A Solvent-Titration Study of Peptides Related to
the C-Terminal Decapeptide Sequence of Porcine Secretin.- Peptides
Structure and Function. Proc. 9th Amer. Pept. Symp. ( Deber, C.M., Hruby,
V.J. and Kopple, K.D., eds.) 1985, Pierce Chem. Co., Rockford, IL.
pp.419-422.

------------------------------------------------
Igor L. Rodionov
Laboratory of Peptide Chemistry
Branch of Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry
Pushchino, Moscow Region
142292, Russian Federation
E-mail: <rodionov@fibkh.serpukhov.su> or <Igor_Rodionov@iname.com>
Fax: (0967)-79-05-27
Phones: (0967) 73 54 42; private: (0967) 73 58 26