Acidic coupling and aminolytic TFA cleavage approaches in a new synthesis of an l- m-sarcolysin containing antitumor tripeptide ester

l-prolyl- l-m-[bis(chloroethyl)amino]-phenylalanyl- l-norvaline ethyl ester hydrochloride, 4 (and its 3H and 14C doublylabeled version) was synthesized starting with reacting unprotected l-m-sarcolysin, 1, with TFA-Pro-Cl in an acidic system to yield TFA-Pro- l-m-sarcolysin, 2, which was transformed...

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Published inTetrahedron letters Vol. 37; no. 5; pp. 563 - 566
Main Authors Weisz, Imre, Roboz, John, George Bekesi, J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.01.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHLORIDES
INVITRO
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Summary:l-prolyl- l-m-[bis(chloroethyl)amino]-phenylalanyl- l-norvaline ethyl ester hydrochloride, 4 (and its 3H and 14C doublylabeled version) was synthesized starting with reacting unprotected l-m-sarcolysin, 1, with TFA-Pro-Cl in an acidic system to yield TFA-Pro- l-m-sarcolysin, 2, which was transformed to the TFA-tripeptide ethyl ester, 3. Selective aminolytic cleavage of the TFA group with butylamine in abs. ethanol, followed by neutralization with HCl gave 4. Synthesis of L-prolyl-L-m-[bis(chloroethyl) amino]-phenylalanyl-L-norvaline ethyl ester HCl from unprotected L-m-sarcolysin is reported using novel approaches.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)02261-9