Synthesis 2017; 49(10): 2187-2204
DOI: 10.1055/s-0036-1588698
paper
© Georg Thieme Verlag Stuttgart · New York

Fluorous Mixture Synthesis of Tripeptides and Pentapeptides Using­ a Fluorous-Fmoc Protection Strategy

Yuya Sugiyama
Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tenpaku-ku, Nagoya, Aichi, Japan   eMail: matsugi@meijo-u.ac.jp
,
Ryuhei Shirai
Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tenpaku-ku, Nagoya, Aichi, Japan   eMail: matsugi@meijo-u.ac.jp
,
Masaki Hirose
Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tenpaku-ku, Nagoya, Aichi, Japan   eMail: matsugi@meijo-u.ac.jp
,
Tomoko Watanabe
Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tenpaku-ku, Nagoya, Aichi, Japan   eMail: matsugi@meijo-u.ac.jp
,
Ayana Yoshida
Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tenpaku-ku, Nagoya, Aichi, Japan   eMail: matsugi@meijo-u.ac.jp
,
Natsuki Endo
Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tenpaku-ku, Nagoya, Aichi, Japan   eMail: matsugi@meijo-u.ac.jp
,
Toshiya Hayashi
Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tenpaku-ku, Nagoya, Aichi, Japan   eMail: matsugi@meijo-u.ac.jp
,
Takayuki Shioiri
Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tenpaku-ku, Nagoya, Aichi, Japan   eMail: matsugi@meijo-u.ac.jp
,
Masato Matsugi*
Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tenpaku-ku, Nagoya, Aichi, Japan   eMail: matsugi@meijo-u.ac.jp
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Publikationsverlauf

Received: 28. November 2016

Accepted after revision: 05. Januar 2017

Publikationsdatum:
06. Februar 2017 (online)


Abstract

A liquid-phase split-type synthesis of various tripeptides and pentapeptides was conducted using a fluorous-Fmoc protection strategy. Fluorous-Fmoc reagents were effectively used as both the protecting group for the amino function and the encoding tag for the amino acid structure. Several of the synthetic peptides prepared showed high activities in an ACE inhibitory assay.

Supporting Information