81323-58-2Relevant articles and documents
An efficient and scalable synthesis of Isodesmosine
Ashish,Chaudhari, Vinod D.,Gupta, Aikan,Nihalani, Deepak,Pawar, Ganesh P.,Sharma, Yogesh
, (2022/02/09)
Isodesmosine is 1,2,3,5-tetrasubstituted pyridinium-based amino acid substituted with four lysine derivatives found in elastin which is the main component of elastic fiber. Elastin plays a vital role in providing stretchy properties to tissues and body organs. Isodesmsoine is a proven to be useful biomarker for elastin degradation during the progressing stage of chronic obstructive pulmonary disease (COPD) and related diseases. The present work reported an efficient and gram-scale approach for the synthesis of Isodesmosine, starting from readily available Boc-Asp-OtBu using mild reaction conditions.
Chemical synthesis of disulfide surrogate peptides by using beta-carbon dimethyl modified diaminodiacids
Bierer, Donald,Cui, Ji-Bin,Li, Yi-Ming,Shi, Jing,Wei, Xiao-Xiong,Zhao, Rui,Zhu, Huixia
supporting information, p. 9021 - 9025 (2021/11/04)
The replacement of disulfide bridges with metabolically stable isosteres is a promising strategy to improve the stability of disulfide-rich polypeptides towards reducing agents and isomerases. A diaminodiacid-based strategy is one of the most effective methods to construct disulfide bond mimics, but modified diaminodiacids have not been developed till now. Inspired by the fact that alkylation of disulfide bonds can regulate the activity of polypeptides, herein, we report the first example of thioether bridged diaminodiacids incorporating Cys Cβdimethyl modification, obtained by penicillamine (Pen)-based thiol alkylation. The utility of these new diaminodiacids was demonstrated by the synthesis of disulfide surrogates of oxytocin containing a short-span disulfide bond and of KIIIA with large-span disulfide bonds. This new type of synthetic bridge further extends the diaminodiacid toolbox to facilitate the study of the structure-activity relationship of disulfide-rich peptides.
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.