Novel fully protected muramic acid: A facile synthesis and structural study (CROSBI ID 194633)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Kovačević, Monika ; Rapić, Vladimir ; Lukač, Iva ; Molčanov, Krešimir ; Kodrin, Ivan ; Barišić, Lidija
engleski
Novel fully protected muramic acid: A facile synthesis and structural study
Synthesis and structural characterisation of novel fully protected muramic acid 2 (N-Boc-Mur-OMe, Mur = muramic acid) has been reported. N-Ac-Mur-OMe (1) prepared starting from commercially available N-acetylglucosamine, was treated with di-tert-butyl dicarbonate (Boc2O) and N, N-dimethyl-4-aminopyridine (DMAP) in tetrahydrofuran. The intermediate mixed imide N-Ac-N-Boc-Mur-OMe was converted to N-Boc-Mur-OMe (2) upon in situ treatment with hydrazine hydrate in methanol. The structural analysis of 2, performed by IR and NMR spectroscopic methods and X-ray crystallography, was augmented by computational calculations including molecular and density functional theory studies (DFT) using M06/6-31G(d) computational model. The spectroscopic and DFT data obtained for novel Boc-protected 2 were compared with corresponding experimental values of its previously described Ac-protected analogue 1 in order to examine if the replacement of the protecting groups influences the conformational properties.
protected muramic acid; structural analysis; X-ray crystallography; DFT calculations
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Podaci o izdanju
1048
2013.
349-356
objavljeno
0022-2860
10.1016/j.molstruc.2013.06.011