Direct evidence for the function of crustacean insulin-like androgenic gland factor (IAG): Total chemical synthesis of IAG

Hidekazu Katayama; Nozomi Kubota; Hironobu Hojo; Ayumi Okada; Sayaka Kotaka; Naoaki Tsutsui; Tsuyoshi Ohira

doi:10.1016/j.bmc.2014.09.031

Direct evidence for the function of crustacean insulin-like androgenic gland factor (IAG): Total chemical synthesis of IAG

Hidekazu Katayama, Nozomi Kubota, Hironobu Hojo, Ayumi Okada, Sayaka Kotaka, Naoaki Tsutsui, Tsuyoshi Ohira

Faculty of Science

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

22 Citations (Scopus)

Abstract

Insulin-like androgenic gland factor (IAG) is presumed to be a sex differentiation factor so-called androgenic gland hormone (AGH) in decapod crustacean, although the function of IAG peptide has not yet been reported. In this study, we synthesized IAG from the prawn, Marsupenaeus japonicus, and its function was assessed by an in vitro bioassay. As a result, IAG with the insulin-type disulfide bond arrangement showed biological activity, whereas its disulfide isomer did not. These results strongly suggest that the native IAG peptide has an insulin-type disulfide, and it is the decapod AGH.

Original language	English
Pages (from-to)	5783-5789
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	22
Issue number	21
DOIs	https://doi.org/10.1016/j.bmc.2014.09.031
Publication status	Published - Nov 1 2014

Keywords

Crustacean
Glycopeptide
Insulin-like androgenic gland factor
Marsupenaeus japonicus
Solid-phase peptide synthesis

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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Direct evidence for the function of crustacean insulin-like androgenic gland factor (IAG) : Total chemical synthesis of IAG. / Katayama, Hidekazu; Kubota, Nozomi; Hojo, Hironobu; Okada, Ayumi; Kotaka, Sayaka; Tsutsui, Naoaki; Ohira, Tsuyoshi.

In: Bioorganic and Medicinal Chemistry, Vol. 22, No. 21, 01.11.2014, p. 5783-5789.

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

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abstract = "Insulin-like androgenic gland factor (IAG) is presumed to be a sex differentiation factor so-called androgenic gland hormone (AGH) in decapod crustacean, although the function of IAG peptide has not yet been reported. In this study, we synthesized IAG from the prawn, Marsupenaeus japonicus, and its function was assessed by an in vitro bioassay. As a result, IAG with the insulin-type disulfide bond arrangement showed biological activity, whereas its disulfide isomer did not. These results strongly suggest that the native IAG peptide has an insulin-type disulfide, and it is the decapod AGH.",

keywords = "Crustacean, Glycopeptide, Insulin-like androgenic gland factor, Marsupenaeus japonicus, Solid-phase peptide synthesis",

author = "Hidekazu Katayama and Nozomi Kubota and Hironobu Hojo and Ayumi Okada and Sayaka Kotaka and Naoaki Tsutsui and Tsuyoshi Ohira",

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T2 - Total chemical synthesis of IAG

AU - Katayama, Hidekazu

AU - Kubota, Nozomi

AU - Hojo, Hironobu

AU - Okada, Ayumi

AU - Kotaka, Sayaka

AU - Tsutsui, Naoaki

AU - Ohira, Tsuyoshi

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N2 - Insulin-like androgenic gland factor (IAG) is presumed to be a sex differentiation factor so-called androgenic gland hormone (AGH) in decapod crustacean, although the function of IAG peptide has not yet been reported. In this study, we synthesized IAG from the prawn, Marsupenaeus japonicus, and its function was assessed by an in vitro bioassay. As a result, IAG with the insulin-type disulfide bond arrangement showed biological activity, whereas its disulfide isomer did not. These results strongly suggest that the native IAG peptide has an insulin-type disulfide, and it is the decapod AGH.

AB - Insulin-like androgenic gland factor (IAG) is presumed to be a sex differentiation factor so-called androgenic gland hormone (AGH) in decapod crustacean, although the function of IAG peptide has not yet been reported. In this study, we synthesized IAG from the prawn, Marsupenaeus japonicus, and its function was assessed by an in vitro bioassay. As a result, IAG with the insulin-type disulfide bond arrangement showed biological activity, whereas its disulfide isomer did not. These results strongly suggest that the native IAG peptide has an insulin-type disulfide, and it is the decapod AGH.

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KW - Glycopeptide

KW - Insulin-like androgenic gland factor

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KW - Solid-phase peptide synthesis

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Direct evidence for the function of crustacean insulin-like androgenic gland factor (IAG): Total chemical synthesis of IAG

Abstract

Keywords

ASJC Scopus subject areas

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