139686-87-6Relevant articles and documents
Biochemical studies of inositol: N -acetylglucosaminyltransferase involved in mycothiol biosynthesis in Corynebacterium diphtheria
Guo, Yuchuan,Wang, Lizhen,Guo, Jiatong,Gu, Guofeng,Guo, Zhongwu
, p. 3775 - 3782 (2017/07/07)
Mycothiol (MSH) is the predominant low molecular weight thiol produced by actinomycetes, and it plays a pivotal role in the bacterial detoxication process. 1L-myo-Inositol-1-phosphate (1L-Ins-1-P) α-N-acetylglucosaminyltransferase (GlcNAc-T), known as MshA, is the only glycosyltransferase involved in MSH biosynthesis. In this work, the MshA from Corynebacterium diphtheria, named as CdMshA, was expressed, purified, and studied in detail. Its enzymatic activity to transfer GlcNAc to 1L-Ins-1-P was confirmed by the isolation and rigorous characterization of its reaction product 3-phospho-1-d-myo-inositol-2-acetamido-2-deoxy-α-d-glucopyranoside. CdMshA was shown to accept only UDP-GlcNAc and 1L-Ins-1-P as its substrates among various tested glycosyl donors, such as UDP-GlcNAc, UDP-Gal, UDP-Glc, UDP-GalNAc and UDP-GlcA, and glycosyl acceptors, such as myo-inositol, 1L-Ins-1-P and 1D-Ins-1-P. The results have demonstrated the strict substrate selectivity of CdMshA. Furthermore, its reaction kinetics with UDP-GlcNAc and 1L-Ins-1-P as substrates were characterized, while site-directed mutagenesis of CdMshA disclosed that its amino acid residues N28, K81 and R157 were essential for its enzymatic activity.
Regioselective functionalizations and conformational studies of di-O-isopropylidene-myo-inositol derivatives
Chung, Sung-Kee,Ryu, Youngha
, p. 145 - 168 (2007/10/02)
(+/-)-1,2:4,5-Di-O-isopropylidene-myo-inositol (5) and (+/-)-1,2:5,6-di-O-isopropylidene-myo-inositol (6) could be regioselectively functionalized in reactions including alkylation, acylation, and silylation at HO-3 in preference to HO-6 and HO-4, respectively, under specific conditions.The presence of intramolecular hydrogen bonding was evident in IR and 1H NMR spectra, and the HO-3 group was identified as the hydrogen-bonding donor in 5 and 6.In their crystalline states, diol 5 prefers a chair conformation and diol 6 a twist boat (skew) conformation.Both compounds appear to have substantial populations of chair conformations in the gas and solution phases, on the basis of the MM-2 energy minimizations and comparisons of vicinal coupling constants observed in the 1H NMR spectra (in CDCl3 and Me2SO-d6) and calculated from the crystal and MM-2 conformations.It is suggested as an explanation for the observed selectivities that the kinetic acidity of the HO-3 group may be enhanced through its intramolecular hydrogen bonding with the cis-vicinal oxygen, or the nucleophilicity of the 3-alkoxide may be enhanced due to its interaction with the cis-vicinal oxygen in a manner similar to the through-space α-effect.
Improved preparation of acetals of myo-inositol and its (+/-)-1-benzyl ether: conformational analysis of di-O-isopropylidene-myo-inositol derivatives
Pradilla, Roberto Fernandez de la,Jaramillo, Carlos,Jimenez-Barbero, Jesus,Martin-Lomas, Manuel,Penades, Soledad,Zapata, Amparo
, p. 249 - 257 (2007/10/02)
The acid-catalysed reactions of myo-inositol with 3-5 equiv. of 2-methoxypropene or 2,2-dimethoxypropane in methyl sulfoxide or N,N-dimethylformamide gave mixtures of the 1,2:4,5-, 1,2:5,6-, and 1,2:3,4-di-O-isopropylidene derivatives with little or none