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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 192, 2017 - Issue 6: Harry Hudson Special Issue
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Original Articles

Michael additions to double bonds of esters of N-protected (s)-phenylalanyldehydroalanine (X-(s)-Phe-ΔAla-OMe) and its phosphonic acid counterpart (X-(s)-Phe-ΔAla-PO(OEt)2)

Paweł LenartowiczFaculty of Chemistry, Opole University, Opole, PolandCorrespondence[email protected]
,
Błażej DziukFaculty of Chemistry, Opole University, Opole, Poland
,
Bartosz ZarychtaFaculty of Chemistry, Opole University, Opole, Poland
,
Maciej MakowskiFaculty of Chemistry, Opole University, Opole, Poland
&
Paweł KafarskiFaculty of Chemistry, Wrocław University of Science and Technology, Wrocław, Poland
Pages 706-712 | Received 30 Jan 2017, Accepted 01 Mar 2017, Published online: 25 May 2017
 
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GRAPHICAL ABSTRACT

ABSTRACT

Electrophilic addition of amines, thiols and bromide to the double bonds of model dehydrodipeptides and dehydrophosphonodipeptide was studied. The double bond in these two classes of peptides reacted similarly and gave the same products. These results indicate that dehydropeptides are very good candidates as substrates for modifications of peptide side-chains.

Funding

Support from the National Science Centre, Poland (Grant 2016/21/B/ST5/00115), is gratefully acknowledged.

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