Total Synthesis and Stereochemical Assignment of Nostosin B.

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.

journal_name

Mar Drugs

journal_title

Marine drugs

authors

Wang X,Feng J,Xu Z,Ye T,Meng Y,Zhang Z

doi

10.3390/md15030058

subject

Has Abstract

pub_date

2017-02-27 00:00:00

issue

3

issn

1660-3397

pii

md15030058

journal_volume

15

pub_type

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