The most recent review on the synthetic aspects of multiply cystine
containing peptides that I know is the ref.1 below.
If my memory works, Synthetic Peptides. (Ref.3) has a chapter on disulfide
bond formation as well.
I hope you will also find useful other relevant references which I
retrieved from my database.
Kindest regards,
Igor Rodionov
1. Andreu, D., Albericio, F., Sole, N.A., Munson, M.C., Ferrer, M. and
Barany, G. Formation of disulfide bonds in synthetic peptides and
proteins.- In: Methods in Molecular Biology, Vol.35. Peptide Synthesis
Protocols. (Pennington, M.W. and Dunn, B.M., eds.), Humana Press, NJ, 1994,
pp.91-169.
2. Musiol, H.J., Siedler, F., Quarzago, D. and Moroder, L. Redox-active
bis-cysteinyl peptides. I. Synthesis of cyclic cystinyl peptides by
conventional methods in solution and on solid supports.- Biopolymers, 1994,
v.34(11), pp.1553-62.
3. Synthetic Peptides. A User's Guide. (Grant G.A., Ed.).- Freeman and
Company: New York, 1992.
4. Chen, L., Zoulikova, I., Slaninova, J. and Barany, G. Synthesis and
pharmacology of novel analogues of oxytocin and deaminooxytocin: directed
methods for the construction of disulfide and trisulfide bridges in
peptides.- J Med Chem, 1997, v.40(6), pp.864-76.
5. Tamamura, H., Otaka, A., Nakamura, J., Okubo, K., Koide, T., Ikeda, K.,
Ibuka, T. and Fujii, N. Disulfide bond-forming reaction using a dimethyl
sulfoxide/aqueous HCl system and its application to regioselective two
disulfide bond formation.- Int J Pept Protein Res, 1995, v.45(4),
pp.312-9.
6. Munson, M.C., Lebl, M., Slaninova, J. and Barany, G. Solid-phase
synthesis and biological activity of the parallel dimer of
deamino-oxytocin.- Pept Res, 1993, v.6(3), pp.155-9.
7. Koide, T., Otaka, A. and Fujii, N. Investigation of the
dimethylsulfoxide-trifluoroacetic acid oxidation system for the synthesis
of cystine-containing peptides.- Chem Pharm Bull(Tokyo), 1993, v.41(6),
pp.1030-4.
8. Albericio, F., Hammer, R.P., Garcia-Echeverria, C., Molins, M.A., Chang,
J.L., Munson, M.C., Pons, M., Giralt, E. and Barany, G. Cyclization of
disulfide-containing peptides in solid-phase synthesis.- Int J Pept Protein
Res, 1991, v.37(5), pp.402-13.
9. Ploux, O., Chassaing, G. and Marquet, A. Cyclization of peptides on a
solid support. Application to cyclic analogs of substance P.- Int J Pept
Protein Res, 1987, v.29(2), pp.162-9.
------------------------------------------------
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
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-----Original message-----------
Dear ABRFers,
I'm looking for the latest and greatest reference on how to form cyclic
peptides through cysteine SH groups when there are are more than two
cysteines present.
I was wondering if the use of ACM to block the unwanted Cys residue,
followed by cyclization, followed by mecury acetate removal of the ACM is
still in vogue or if there is a better protecting group or strategy
available.
Thanks in advance,
Dick Cook