Chemical Synthesis of α-d-Mannosylphosphate Serine Derivatives: A New Class of Synthetic Glycopeptides

Synlett ◽  
2003 ◽  
Vol 2003 (09) ◽  
Author(s):  
Geert-Jan Boons ◽  
Galal Elsayed
Keyword(s):  
2014 ◽  
Vol 10 ◽  
pp. 1564-1569 ◽  
Author(s):  
Sebastian Rabe ◽  
Johann Moschner ◽  
Marina Bantzi ◽  
Philipp Heretsch ◽  
Athanassios Giannis

The chemical synthesis of carbacyclopamine analog 2, a cyclopamine analog with an all-carbon E-ring, is reported. The use of C–H-functionalization logic and further metal-catalyzed transformations allows for a concise entry to this new class of acid-stable cyclopamine analogs.


1968 ◽  
Vol 46 (3) ◽  
pp. 525-532 ◽  
Author(s):  
Erich Baer ◽  
Bimal C. Pal

The first chemical synthesis of a dihydroceramide aminoethylphosphonate is described. It is a saturated representative of a new class of recently discovered, naturally occurring complex lipids derived from phosphonic acid. The compound, viz. erythro-N-palmitoyl-DL-dihydrosphingosyl-1-(2-aminoethyl)-phosphonate, was obtained by two procedures: phosphonylation of erythro-N-palmitoyl-3-O-benzoyl-DL-dihydrosphingosine with (2-N,N-dibenzylammoethyl)phosphonic acid chloride (hydrochloride) and triethylamine, or with (2-phthalimidoethyl)phosphonic acid monochloride and triethylamine, and freeing the reaction products of both procedures, viz. erythro-N-palmitoyl-3-O-benzoyl-DL-dihydrosphingosyl-1-(2-N,N-dibenzylaminoethyl)phosphonate and erythro-N-palmitoyl-3-O-benzoyl-DL-dihydrosphingosyl-1-(2-phthalimidoethyl)phosphonate, from their protective benzyl or phthaloyl group by hydrogenolysis or hydrazinolysis, respectively, followed in both cases by removal of the benzoyl group by saponification.The (2-N,N-dibenzylaminoethyl)phosphonic acid was obtained by treating (2-bromoethyl)phosphonic acid with N,N-dibenzylamine and converting the reaction product, viz. the dibenzylammonium salt of (2-N,N-dibenzylaminoethyl)phosphonic acid, into the free acid by steam distillation.


1996 ◽  
Vol 4 (9) ◽  
pp. 1545-1558 ◽  
Author(s):  
Earl E. Rutenber ◽  
Fiona McPhee ◽  
Alan P. Kaplan ◽  
Steven L. Gallion ◽  
Joseph C. Hogan ◽  
...  

Marine Drugs ◽  
2017 ◽  
Vol 15 (9) ◽  
pp. 288 ◽  
Author(s):  
Emiliano Manzo ◽  
Laura Fioretto ◽  
Dario Pagano ◽  
Genoveffa Nuzzo ◽  
Carmela Gallo ◽  
...  

2021 ◽  
Author(s):  
M Rejzek ◽  
Tung B. K. Le

AbstractSlowly- or non-hydrolyzable analogs of ATP and GTP, for example adenosine 5’-(γ-thio)triphosphate (ATPγS) and guanosine 5’-(γ-thio)triphosphate (GTPγS), have been widely employed to probe the roles of ATP and GTP in biosystems, and these compounds are readily available from commercial sources. In contrast, cytosine 5’-(γ-thio)triphosphate (CTPγS) is not widely available commercially. The recent discovery of ParB as the founding member of a new class of CTPase enzyme (Osorio-Valeriano et al., 2019; Soh et al., 2019) and the possibility of multiple other undiscovered CTPases necessitate the use of the CTPγS to elucidate the roles of CTP hydrolysis in these systems. Here, we adapt a procedure for the synthesis of modified phosphoanhydrides (Hofer et al., 2015) to chemically synthesize and purify a milligram-scale of CTPγS.


2019 ◽  
Vol 27 (8) ◽  
pp. 1489-1496
Author(s):  
Qianqian Liu ◽  
Xia Li ◽  
Yong-Sheng Bao ◽  
Jingxin Lu ◽  
Hua Li ◽  
...  

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