Alkhzem Abdulaziz H, Woodman Timothy J, Blagbrough Ian S
Department of Pharmacy and Pharmacology, University of Bath, Bath BA2 7AY, U.K.
ACS Omega. 2021 Jan 20;6(4):2824-2835. doi: 10.1021/acsomega.0c05138. eCollection 2021 Feb 2.
Unambiguous assignments have been made for each individual p value of the amino group and guanidine substituents on 2-deoxystreptamine, neamine, neomycin, paromomycin, and streptomycin by pH-titration evaluation of their H, C, and N (by H-N heteronuclear multiple-bond correlation (HMBC) spectra) NMR chemical shifts (δs) 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 p value of the similar amine and guanidine functional groups, which decorate aminoglycoside antibiotics.
通过对2-脱氧链霉胺、新霉素、新霉素、巴龙霉素和链霉素上氨基和胍取代基的每个单独pKa值进行pH滴定评估，以其H、C和N（通过H-N异核多键相关（HMBC）光谱）NMR化学位移（δs）作为报告核，已明确指定了这些值。这些数据需要对新霉素和巴龙霉素的文献数据在分配顺序方面进行细微修订。原位滴定和NMR光谱显示是一种强大的组合，可快速（几分钟）获得修饰氨基糖苷类抗生素的类似胺和胍官能团的每个不同pKa值。
