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Mar. Drugs 2017, 15(3), 58; doi:10.3390/md15030058

Total Synthesis and Stereochemical Assignment of Nostosin B

1
School of Life Science, Jiangxi Science and Technology Normal University, Nanchang 330013, China
2
Laboratory of Chemical Genomics, Engineering Laboratory for Chiral Drug Synthesis, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, University Town of Shenzhen, Xili, Nanshan District, Shenzhen 518055, China
3
State Intellectual Property Office of the People’s Republic of China, Kaiyuan Road, Guang Zhou 510000, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Orazio Taglialatela‐Scafati
Received: 13 January 2017 / Accepted: 22 February 2017 / Published: 27 February 2017
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Abstract

Nostosins A and B were isolated from a hydrophilic extract of Nostoc sp. strain from Iran, which exhibits excellent tryps inhibitory activity. Nostosin A was the most potent natural tripeptide aldehyde as trypsin inhibitor up to now. Both R‐ and S‐2‐hydroxy‐4‐(4‐hydroxy‐phenyl) butanoic acid (Hhpba) were prepared and incorporated into the total synthesis of nostosin B, respectively. Careful comparison of the NMR spectra and optical rotation data of synthetic nostosin B (1a and 1b) with the natural product led to the unambiguous identification of the R‐configuration of the Hhpba fragment, which was further confirmed by co‐injection with the authentic sample on HPLC using both reversed phase column and the chiral AD‐RH column. View Full-Text
Keywords: nostosin B; total synthesis; stereochemical assignment nostosin B; total synthesis; stereochemical assignment
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Wang, X.; Feng, J.; Xu, Z.; Ye, T.; Meng, Y.; Zhang, Z. Total Synthesis and Stereochemical Assignment of Nostosin B. Mar. Drugs 2017, 15, 58.

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