公开(公告)号：US20210122781A1

公开(公告)日：2021-04-29

申请号：US16497301

申请日：2018-03-26

申请人： Agency for Science, Technology and Research

发明人： Tsz Ying Yuen ,  Charles William Johannes ,  Fernando Jose Ferrer Gago

IPC分类号： C07K1/113

摘要： This invention relates to a process for producing a compound of Formula I, comprising: 1) performing a stereoselective metathesis reaction on a compound of Formula II so as to form an intramolecular alkenyl chain, and 2) cleaving S from P2 so as to produce a compound of Formula I. A product containing an (Z)- or (E)-olefin isomer stabilised in an a-helical conformation is obtained by the said process.

公开(公告)号：US20200031760A1

公开(公告)日：2020-01-30

申请号：US16497299

申请日：2018-03-23

申请人： Agency for Science, Technology and Research

发明人： Tsz Ying Yuen ,  Charles William Johannes ,  Greg Verdins

IPC分类号： C07C227/12 ,  C07C229/48 ,  C07D265/32 ,  C07D265/34 ,  C07K5/08 ,  C07K7/06

摘要： This invention relates to a method for producing an alkenyl 1-aminocyclopropane-1-carboxylic acid of Formula I wherein R1 is a protecting group, n is an integer between 1 and 10, and A and B are chiral centres such that when A is S, B is R and when A is R, B is S. The method comprises a stereoselective formation of the cyclopropane moiety by cycloaddition onto a double bond, in a molecule comprising a chiral template, Formula lc. Further provided is the use of Formula I in the production of stapled peptides.

公开(公告)号：US11236128B2

公开(公告)日：2022-02-01

申请号：US16635472

申请日：2018-07-31

申请人： Agency for Science, Technology and Research

发明人： Tsz Ying Yuen ,  Charles William Johannes ,  Gerard Hilinski

IPC分类号： C07K7/08 ,  C01G55/00 ,  C07K1/04 ,  C07K1/12

摘要： Described herein is an operationally simple, one-pot solid-supported preparation of saturated stapled peptides. Following completion of ruthenium-catalysed metathesis, solid-phase transfer hydrogenation was achieved using triethylhydrosilane at elevated temperatures. The utility of the method has been demonstrated on 14- and 16-mer peptides to yield the corresponding cyclic a-helix stabilised stapled peptides.

公开(公告)号：US11091427B2

公开(公告)日：2021-08-17

申请号：US16497299

申请日：2018-03-23

申请人： Agency for Science, Technology and Research

发明人： Tsz Ying Yuen ,  Charles William Johannes ,  Greg Verdine

IPC分类号： C07C227/12 ,  C07C229/48 ,  C07D265/32 ,  C07D265/34 ,  C07K5/08 ,  C07K7/06

摘要： This invention relates to a method for producing an alkenyl 1-aminocyclopropane-1-carboxylic acid of Formula I wherein R1 is a protecting group, n is an integer between 1 and 10, and A and B are chiral centres such that when A is S, B is R and when A is R, B is S. The method comprises a stereoselective formation of the cyclopropane moiety by cycloaddition onto a double bond, in a molecule comprising a chiral template, Formula lc. Further provided is the use of Formula I in the production of stapled peptides.