The effect of sulfur stereochemistry of l-β,β-dimethylmethionine S-oxide on the physicochemical properties of truncated polytheonamides

Shigeru Matsuoka; Yuki Mizoguchi; Hiroaki Itoh; Ken Okura; Naoki Shinohara; Masayuki Inoue

doi:10.1016/j.tetlet.2010.06.126

The effect of sulfur stereochemistry of l-β,β-dimethylmethionine S-oxide on the physicochemical properties of truncated polytheonamides

Shigeru Matsuoka, Yuki Mizoguchi, Hiroaki Itoh, Ken Okura, Naoki Shinohara, Masayuki Inoue

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

L-β,β-Dimethylmethionine S-oxide is a unique amino acid found in polytheonamides. Four designed hexapeptides containing the sulfide, (S _R)-sulfoxide, (S_S)-sulfoxide, and sulfone derivatives of l-dimethylmethionine were synthesized and functionally analyzed. Our results indicate that the sulfoxide stereochemistry of the peptides controls their overall physicochemical properties.

Original language	English
Pages (from-to)	4644-4647
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2010.06.126
Publication status	Published - 2010 Sept 1

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.06.126

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abstract = "L-β,β-Dimethylmethionine S-oxide is a unique amino acid found in polytheonamides. Four designed hexapeptides containing the sulfide, (S R)-sulfoxide, (SS)-sulfoxide, and sulfone derivatives of l-dimethylmethionine were synthesized and functionally analyzed. Our results indicate that the sulfoxide stereochemistry of the peptides controls their overall physicochemical properties.",

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T1 - The effect of sulfur stereochemistry of l-β,β-dimethylmethionine S-oxide on the physicochemical properties of truncated polytheonamides

AU - Matsuoka, Shigeru

AU - Mizoguchi, Yuki

AU - Itoh, Hiroaki

AU - Okura, Ken

AU - Shinohara, Naoki

AU - Inoue, Masayuki

PY - 2010/9/1

Y1 - 2010/9/1

N2 - L-β,β-Dimethylmethionine S-oxide is a unique amino acid found in polytheonamides. Four designed hexapeptides containing the sulfide, (S R)-sulfoxide, (SS)-sulfoxide, and sulfone derivatives of l-dimethylmethionine were synthesized and functionally analyzed. Our results indicate that the sulfoxide stereochemistry of the peptides controls their overall physicochemical properties.

AB - L-β,β-Dimethylmethionine S-oxide is a unique amino acid found in polytheonamides. Four designed hexapeptides containing the sulfide, (S R)-sulfoxide, (SS)-sulfoxide, and sulfone derivatives of l-dimethylmethionine were synthesized and functionally analyzed. Our results indicate that the sulfoxide stereochemistry of the peptides controls their overall physicochemical properties.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

The effect of sulfur stereochemistry of l-β,β-dimethylmethionine S-oxide on the physicochemical properties of truncated polytheonamides

Abstract

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