Gualamycin, a Novel Acaricide Produced by Streptomyces sp. NK11687 II. Structural Elucidation

KOUICHI TSUCHIYA; SFFINICHI KOBAYASHI; TAKASHI KUROKAWA; TAIZO NAKAGAWA; NOBUYOSHI SHIMADA; HIKARU NAKAMURA; YOICHI IITAKA; MASAYUKI KITAGAWA; KUNIAKI TATSUTA

doi:10.7164/antibiotics.48.630

Gualamycin, a Novel Acaricide Produced by Streptomyces sp. NK11687

II. Structural Elucidation

KOUICHI TSUCHIYA, SFFINICHI KOBAYASHI, TAKASHI KUROKAWA, TAIZO NAKAGAWA, NOBUYOSHI SHIMADA, HIKARU NAKAMURA, YOICHI IITAKA, MASAYUKI KITAGAWA, KUNIAKI TATSUTA

Author information

KOUICHI TSUCHIYA
Applied Microbiology Research Center, Nippon Kayaku Co. Ltd.
SFFINICHI KOBAYASHI
Applied Microbiology Research Center, Nippon Kayaku Co. Ltd.
TAKASHI KUROKAWA
Applied Microbiology Research Center, Nippon Kayaku Co. Ltd.
TAIZO NAKAGAWA
Applied Microbiology Research Center, Nippon Kayaku Co. Ltd.
NOBUYOSHI SHIMADA
Applied Microbiology Research Center, Nippon Kayaku Co. Ltd.
HIKARU NAKAMURA
Institute of Microbial Chemistry
YOICHI IITAKA
The Department of Biological Sciences, The Nishi Tokyo University
MASAYUKI KITAGAWA
Waseda University, Graduate School of Science and Engineering
KUNIAKI TATSUTA
Waseda University, Graduate School of Science and Engineering

JOURNAL FREE ACCESS

1995 Volume 48 Issue 7 Pages 630-634

DOI https://doi.org/10.7164/antibiotics.48.630

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Abstract

A novel acaricide, gualamycin was isolated from the culture broth of Streptomyces sp. NK11687. The structure of gualamycin was determined to be (2R, 3S, 4S)-2-O-[4-O-(2-amino-2-deoxy-β-D-gulopyranosyl)-a-D-galactopyranosyl]-2, 3, 4-trihydroxy-4-[(2S, 3S, 4S, 5S)-3, 4-dihydroxy-5-hydroxymethylpyrrolidin-2-yl] butanoic acid by FAB-MS, ¹H and ¹³C NMR, COSY, HMQC, HMBC, IR, X-ray crystallographic analyses and synthetic studies.

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