Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1978-04-28
1979-05-01
Phillips, Delbert R.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
C07C10352
Patent
active
041523229
ABSTRACT:
Nitroarginyl peptides are selectively reduced to the corresponding arginyl peptides by titanium (III). The nitro protecting group which is labile toward nucleophilic reagents is retained through part of a synthesis and selectively removed prior to treatment with nucleophiles such as hydrazine and ammonia. The selectivity of titanium (III) for removal of the nitro functionality increases the flexibility of this protecting group in the synthesis of arginyl peptides. The present novel process is useful in the synthesis of medicinal peptides such as molluscan cardiac stimulant H-Phe-Met-Arg-Phe-NH.sub.2.
REFERENCES:
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J. E. McMurry, et al., J. Org. Chem. 40, 1502 (1975).
P. M. Scopes, et al., J. Chem. Soc. 782 (1965).
A. Turan, et al., Acta Chimica Academiae Scientiarum Hungaricae, 85, 327 (1975).
T. Hayakawa, et al., Bull. Chem. Soc. Jap., 40, 1205 (1967).
S. Sakakibara, et al., Bull. Chem. Soc. Jap., 41, 438 (1968).
M. Bodanzky et al., Peptides Synthesis, 2nd Edition, John Wiley & sons, N.Y., 67-68 (1976).
Merck & Co. , Inc.
Patton Walter
Phillips Delbert R.
Westlake, Jr. Harry E.
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