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Multinuclear Nuclear Magnetic Resonance Spectroscopy Is Used to Determine Rapidly and Accurately the Individual pKa Values of 2-Deoxystreptamine, Neamine, Neomycin, Paromomycin, and Streptomycin
ACS Omega ( IF 4.1 ) Pub Date : 2021-01-20 , DOI: 10.1021/acsomega.0c05138
Abdulaziz H. Alkhzem 1 , Timothy J. Woodman 1 , Ian S. Blagbrough 1
Affiliation  

Unambiguous assignments have been made for each individual pKa value of the amino group and guanidine substituents on 2-deoxystreptamine, neamine, neomycin, paromomycin, and streptomycin by pH-titration evaluation of their 1H, 13C, and 15N (by 1H-15N heteronuclear multiple-bond correlation (HMBC) spectra) NMR chemical shifts (δXs) as the reporter nuclei. These data require minor revisions of the literature data in terms of the assignment order for neomycin and paromomycin. In situ titrations and NMR spectroscopy are shown to be a powerful combination for rapidly (minutes) obtaining each distinct pKa value of the similar amine and guanidine functional groups, which decorate aminoglycoside antibiotics.

中文翻译:

多核核磁共振波谱用于快速准确地确定2-脱氧链胺胺,神经胺,新霉素,巴龙霉素和链霉素的单个p K a

通过对1 H,13 C和15 N的pH滴定评估,对每个个体p K2- K脱氧链胺胺,神经胺,新霉素,巴龙霉素和链霉素的氨基和胍基取代基进行了明确赋值1 H- 15 ñ异核多键相关(HMBC)光谱)NMR化学位移(δ X或多个)作为报道核。这些数据需要根据新霉素和巴龙霉素的分配顺序对文献数据进行较小的修改。原位滴定和NMR光谱显示了快速(分钟)获得每种不同p K a的强大组合 修饰氨基糖苷类抗生素的类似胺和胍官能团的价值
更新日期:2021-02-02
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