A one-pot synthesis of symmetrical and unsymmetrical dipeptide ureas

We gratefully acknowledge financial support from the BBSRC (Grant no. BB/I022910/1 and the European Commission (Seventh Framework Programme, Collaborative project "BlueGenics", Grant no. 311848).We describe a flexible and high yielding synthesis of 1,3-disubstituted ureas, that allows for the construction of both symmetrical and unsymmetrical dipeptide ureas, including easy access to 13C labelled ureas, from amino acids and carbon dioxide at atmospheric pressure.PostprintPostprintPeer reviewe

Synthesis and conformational analysis of fluorinated uridine analogues provide insight into a neighbouring-group participation mechanism

Funding: This work was supported by the EPSRC council (Grant number 1398501) and GlaxoSmithKline.Fluorinated nucleoside analogues have attracted much attention as anticancer and antiviral agents and as probes for enzymatic function. However, the lack of direct synthetic methods, especially for 2′,3′-dideoxy-2′,3′-difluoro nucleosides, hamper their practical utility. In order to design more efficient synthetic methods, a better understanding of the conformation and mechanism of formation of these molecules is important. Herein, we report the synthesis and conformational analysis of a 2′,3′-dideoxy-2′,3′-difluoro and a 2′-deoxy-2′-fluoro uridine derivative and provide an insight into the reaction mechanism. We suggest that the transformation most likely diverges from the SN1 or SN2 pathway, but instead operates via a neighbouring-group participation mechanism.Publisher PDFPeer reviewe

Studies towards the synthesis of (S)-tyrosine based calix[4]arenes and innovative synthetic protocols towards para-tert-butylcalix[n]arenes

EThOS - Electronic Theses Online ServiceGBUnited Kingdo

Studies towards the synthesis of (S)-tyrosine based calix[4]arenes and innovative synthetic protocols towards para-tert-butylcalix[n]arenes

EThOS - Electronic Theses Online ServiceGBUnited Kingdo

Natural products incorporating pyrimidine nucleosides

The uridyl peptide antibiotics are a class of structurally and biologically diverse series of pyrimidine containing natural products, that have attracted considerable interest due to their powerful and varied bioactivities; and potential for exploitation in human medicine as well as agriculture.This article overviews the varied structures of the pyrimidine nucleoside-based antibiotics, their natural origins and their bioactivities. Current understanding of the enzyme mediated assemblies (biosynthesis) of these structurally intriguing compounds is overviewed.</p

Natural products incorporating pyrimidine nucleosides

The uridyl peptide antibiotics are a class of structurally and biologically diverse series of pyrimidine containing natural products, that have attracted considerable interest due to their powerful and varied bioactivities; and potential for exploitation in human medicine as well as agriculture.This article overviews the varied structures of the pyrimidine nucleoside-based antibiotics, their natural origins and their bioactivities. Current understanding of the enzyme mediated assemblies (biosynthesis) of these structurally intriguing compounds is overviewed.</p

Synthesis and conformational analysis of fluorinated uridine analogues provide insight into a neighbouring-group participation mechanism

Fluorinated nucleoside analogues have attracted much attention as anticancer and antiviral agents and as probes for enzymatic function. However, the lack of direct synthetic methods, especially for 2′,3′-dideoxy-2′,3′-difluoro nucleosides, hamper their practical utility. In order to design more efficient synthetic methods, a better understanding of the conformation and mechanism of formation of these molecules is important. Herein, we report the synthesis and conformational analysis of a 2′,3′-dideoxy-2′,3′-difluoro and a 2′-deoxy-2′-fluoro uridine derivative and provide an insight into the reaction mechanism. We suggest that the transformation most likely diverges from the SN1 or SN2 pathway, but instead operates via a neighbouring-group participation mechanism