Synthesis of biopterin and related pterin glycosides

Abstract

Certain pterins having a hydroxyalkyl side chain at C-6 have been found as glycosidic forms in certain prokaryotes, such as 2'-O-(α-D-glucopyranosyl)biopterin from various kinds of cyanobacteria, and limipterin from a green sulfur photosynthetic bacterium. Synthetic studies on glycosides of biopterin and related pterins have been made in view of the structural proof as well as for closer examination of their biological activities and functions. The syntheses of these natural pterin glycosides have effectively been achieved, mostly through appropriately protected N(2) -(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]pterin derivatives as glycosyl acceptors, and are reviewed here.

Enhanced Wound Healing Potential of Spirulina platensis Nanophytosomes: Metabolomic Profiling, Molecular Networking, and Modulation of HMGB-1 in an Excisional Wound Rat Model

“…Two nodes of one nucleotide and one nucleoside were annotated, representing guanosine monophosphate and deoxyguanosine, respectively. Moreover, one cluster contained pterin, a known biomolecule synthesized by S. platensis [ 22 ]. Another cluster represented a node with an oxylipin, 12,13-dihydroxy-9Z-octadecenoic acid (12,13-DiHOME) [ 23 ].…”

Tetrahydrobiopterin from cyanide‐degrading bacterium Bacillus pumilus strain SVD06 induces apoptosis in human lung adenocarcinoma cell (A549)

“…From the H‐NMR and fast‐atom bombardment mass spectrometry analysis, the identified compounds were found to be as tatiopterin‐ O and thermopterin. Similarly, 2′‐ O ‐(α‐ d ‐glucopyranosyl) biopterin from various kinds of cyanobacteria, and limipterin from a green sulfur photosynthetic bacterium were isolated by 40 …”

“…Similarly, 2′-O-(α-d-glucopyranosyl) biopterin from various kinds of cyanobacteria, and limipterin from a green sulfur photosynthetic bacterium were isolated by. 40 The MTT assay is a commonly used method to assess cell viability based on the activity of mitochondrial dehydrogenases in viable cells. These enzymes have the ability to cleave the tetrazolium rings forming a dark blue membrane-impermeable crystal of formazan.…”

Bicyclic 6-6 Systems: Pteridines

“…The syntheses of natural pterin glycosides are commonly achieved through appropriately protected N 2 -(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]pterin derivatives as glycosyl acceptors. 130 Synthesis of tetrahydrobiopterin 45 analogues is also recently reported. 131 The synthesis of cyclic pyranopterin monophosphate cPMP…”