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Title of Journal: Amino Acids

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Abbravation: Amino Acids

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Springer Vienna

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DOI

10.1007/bf00478905

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ISSN

1438-2199

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Pitfalls in the synthesis of fluorescent methotrex

Authors: Mónika Sebestyén György Kóczán Ferenc Hudecz
Publish Date: 2016/06/29
Volume: 48, Issue: 11, Pages: 2599-2604
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Abstract

Methotrexate MTX conjugates with polyLysDLAlam based polymeric polypeptides are efficient against Leishmania donovani parasite infection but the mechanism of the effect is not known yet We prepared therefore the 56carboxyfluorescein Cf labeled oligopeptide CfKAaAa a Dalanine A Lalanine and the corresponding MTX conjugates CfKMTXAaAa as model compounds for structure–activity experiments The conjugate aimed to be synthesized with solid phase methodology on MBHA resin with Boc strategy using FmocLysBocOH However various side reactions were identified Here we report three problems observed during the synthesis as well as solutions developed by us 1 unexpected cyclopeptideformation with the lactonecarboxylic group of the Cf was detected when Cf was attached to the αamino group of the Lys residue on solid phase This was avoided by changing the order of Cf incorporation with using Fmoc/Dde strategy Alternatively we have built the peptide with Fmoc strategy on solid phase first and performed the labeling with CfOSu subsequently in solution 2 During HF cleavage of the protected conjugates MTX was demonstrated to form adducts with anisole and pcresol scavengers and the TMSOTf cleavage methodology was also found to be inadequate due to the large number of side products formed We report here that using Fmoc/Dde strategy is an appropriate method to circumvent the cleavage with HF or TMSOTf 3 During the coupling of MTX with oligopeptide structural and stereo isomers are formed We have described here the suitable conditions of HPLC separation of these products

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