Process for producing triglycyl-lysine vasopressin and intermedi

Details Process for producing triglycyl-lysine vasopressin and intermedi Process for producing triglycyl-lysine vasopressin and intermedi

1977-01-31

1978-06-06

Phillips, Delbert R.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07C10352, C07G 700, C09H 0000

Patent

active

040936104

ABSTRACT:
A new process for preparing the cyclic dodecapeptide triglycyl-lysine vasopressin of the formula ##STR1## which comprises the preparation of a first hexapeptide of formula Boc--Gly--Gly--Gly--Cys(Trt)--Tyr--Phe--NHNH.sub.2 and a second hexapeptide of formula H--Gln(Mbh)--Asn(Mbh)--Cys(Trt)--Pro--Lys(Boc)--Gly--NH.sub.2 by a series of condensations involving the reaction of an appropriately protected peptide unit having an activated carboxyl with an appropriately protected peptide having a free amino group. Subsequently, the first and second hexapeptides are condensed according to the azide coupling method to obtain the linear protected dodecapeptide of formula Boc--Gly--Gly--Gly--Cys(Trt)--Tyr--Phe--Gln(Mbh)--Asn(Mbh)--Cys(Trt)--Pro- -Lys(Boc)--Gly--NH.sub.2 ; thereafter the linear protected dodecapeptide is transformed into the desired cyclic dodecapeptide, triglycyllysine vasopressin, by oxidizing and deprotecting processes.

REFERENCES:
patent: 3232923 (1966-02-01), Boissonnas et al.
patent: 3299036 (1967-01-01), Boissonnas et al.
patent: 3371080 (1968-02-01), Boissonnas et al.
Kasofirek, et al., Coll. Czech. Chem. Commun., 31, 4581-4591, 1966.

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