Effect of stereochemistry on the catalytic activity of flavopeptides

Yukihiro Arakawa; Nao Takechi; Ken Yamanomoto; Keiji Minagawa; Yasushi Imada

doi:10.1016/j.tetlet.2021.153107

Effect of stereochemistry on the catalytic activity of flavopeptides

Yukihiro Arakawa
, Nao Takechi
, Ken Yamanomoto
, Keiji Minagawa
, Yasushi Imada

化学科

研究成果: Article › 査読

4 被引用数 (Scopus)

抄録

The original flavopeptide catalyst, 3-FlC2-L-Pro-L-Tyr-L-Asp-Ado-NH-PS (Fl-Pep^LLL), and its diastereomers including Fl-Pep^DDL, Fl-Pep^LDL, and Fl-Pep^DLL were synthesized to investigate the correlation between their catalytic activity and stereochemistry. The results and related computations showed the importance of intramolecular hydrogen bonds involving the Asp residue in their 4a-hydroperoxy forms for the catalysis.

本文言語	English
論文番号	153107
ジャーナル	Tetrahedron Letters
巻	73
DOI	https://doi.org/10.1016/j.tetlet.2021.153107
出版ステータス	Published - 8 6月 2021

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title = "Effect of stereochemistry on the catalytic activity of flavopeptides",

abstract = "The original flavopeptide catalyst, 3-FlC2-L-Pro-L-Tyr-L-Asp-Ado-NH-PS (Fl-PepLLL), and its diastereomers including Fl-PepDDL, Fl-PepLDL, and Fl-PepDLL were synthesized to investigate the correlation between their catalytic activity and stereochemistry. The results and related computations showed the importance of intramolecular hydrogen bonds involving the Asp residue in their 4a-hydroperoxy forms for the catalysis.",

keywords = "Aerobic oxidation, DFT calculation, Flavin, Peptide",

author = "Yukihiro Arakawa and Nao Takechi and Ken Yamanomoto and Keiji Minagawa and Yasushi Imada",

note = "Publisher Copyright: {\textcopyright} 2021 Elsevier Ltd",

year = "2021",

month = jun,

day = "8",

doi = "10.1016/j.tetlet.2021.153107",

language = "English",

volume = "73",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Effect of stereochemistry on the catalytic activity of flavopeptides

AU - Arakawa, Yukihiro

AU - Takechi, Nao

AU - Yamanomoto, Ken

AU - Minagawa, Keiji

AU - Imada, Yasushi

PY - 2021/6/8

Y1 - 2021/6/8

N2 - The original flavopeptide catalyst, 3-FlC2-L-Pro-L-Tyr-L-Asp-Ado-NH-PS (Fl-PepLLL), and its diastereomers including Fl-PepDDL, Fl-PepLDL, and Fl-PepDLL were synthesized to investigate the correlation between their catalytic activity and stereochemistry. The results and related computations showed the importance of intramolecular hydrogen bonds involving the Asp residue in their 4a-hydroperoxy forms for the catalysis.

AB - The original flavopeptide catalyst, 3-FlC2-L-Pro-L-Tyr-L-Asp-Ado-NH-PS (Fl-PepLLL), and its diastereomers including Fl-PepDDL, Fl-PepLDL, and Fl-PepDLL were synthesized to investigate the correlation between their catalytic activity and stereochemistry. The results and related computations showed the importance of intramolecular hydrogen bonds involving the Asp residue in their 4a-hydroperoxy forms for the catalysis.

KW - Aerobic oxidation

KW - DFT calculation

KW - Flavin

KW - Peptide

UR - https://www.scopus.com/pages/publications/85105353774

U2 - 10.1016/j.tetlet.2021.153107

DO - 10.1016/j.tetlet.2021.153107

M3 - Article

AN - SCOPUS:85105353774

SN - 0040-4039

VL - 73

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 153107

ER -

Effect of stereochemistry on the catalytic activity of flavopeptides

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