59768-74-0Relevant articles and documents
Stereoselective Synthesis of Protected l - Allo -Enduracididine and l -Enduracididine via Asymmetric Nitroaldol Reaction
Doi, Takayuki,Ganesan, A.,Masuda, Yuichi,Ohsawa, Kosuke,Thomas, Carys,Tokunaga, Takuya,Zhao, Hongbin
supporting information, p. 942 - 948 (2020/03/23)
The diastereoselecetive and scalable synthesis of cyclic guanidine-containing nonproteinoginic amino acids, enduracididines, has been achieved. Both diastereomers, l - allo -enduracididine and l -enduracididine, were prepared via catalyst-controlled asymmetric nitroaldol reaction with the aldehyde precursor derived from l -aspartic acid. The cyclic guanidine of di-Cbz-protected l - allo -enduracididine was fully protected with an allyl group to suppress nucleophilic side reactions. Introduced allyl group was efficiently removed via π-allylpalladium chemistry without attaching the Cbz group on the cyclic guanidine moiety.
Process for preparing deuterated desmosine and derivatives thereof
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Page/Page column 6; 7; 10, (2019/05/18)
There is provided a process for preparing a compound represented by the following general formula (1) or a salt thereof, which comprises exchanging one or more of an amino proton in a compound represented by the following general formula (2) or a salt thereof to deuterium, and after the exchanging, converting a deuterium-exchanged compound of the compound represented by the general formula (2) or a salt thereof into the compound represented by the general formula (1) or a salt thereof: wherein, in the general formula (1), one, or two or more of hydrogen atom may be substituted with their isotope; and in the general formula (2), each of R1 is independently hydrogen atom, tert-butyloxycarbonyl group or benzyloxycarbonyl group, and R2 is independently tert-butyl group, benzyl group, methyl group or ethyl group.
Synthesis of desmosine-d4: Improvement of isotopic purity by D-H exchange of amino groups
Watanabe, Daisuke,Suzuki, Rina,Usuki, Toyonobu
supporting information, p. 1194 - 1197 (2017/03/02)
Desmosine is a crosslinking pyridinium amino acid of elastin, which is a useful biomarker for the diagnosis of chronic obstructive pulmonary disease (COPD) by LC–MS/MS analysis. We previously reported a synthesis of desmosine-d4, which is useful as an internal standard for quantitative LC–MS/MS analysis of desmosines, by deuterogenation of an alkyne group; however, the isotopic purity of the desmosine-d4was only ca. 50%. The present report describes a new synthesis of desmosine-d4that improves the isotopic purity to ca. 90% by exchanging the protons of the amino groups to deuterium using deuterogenation.