Kirin Brewery

Technical Eeport of Kirin, No. 32, Kirin Brewery Co. Ltd., Tokyo, 1989. 

Kirin Brewery Co., Ltd., (ed.), Biru no Umasa wo Saguru [Study of Deliciousness of Beer], Shokabo, Tokyo, 1992, p.81 [in Japanese]. 

Agelasphin 9b (81) and its relatives were isolated from the Okinawan marine sponge Agelas mauritianus as glycosphingolipids and they exhibited anticancer activity in vivo in mice and humans.56 By simplifying the structure of 81, researchers at Kirin Brewery Co. developed KRN7000 (82) as an anticancer drug candidate.57... 

Figure 3.9 summarizes our synthesis of the enantiomers of JH I in 1988.28 If we want to employ the same strategy as used for the synthesis of JH III, the synthesis of JH I demands the execution of the diastereo-and enantioselective reduction of a prochiral 1,3-diketone A. Unfortunately, reduction of A with fermenting baker s yeast was nondiastereoselective, giving both B and C. After extensive screening of yeasts, Pichia terricola KI 0117 donated by Kirin Brewery Co. was found to achieve highly stereoselective reduction to give >99% of B with 99% ee. Since both of the 3,5-dinitrobenzoates D and E were crystalline, these could be purified by recrystallization, and 100% pure E was secured. Conversion of E to F was achieved by methanolysis followed by acetonide formation. The enantiomeric purity of F was proved to be ca. 100% ee by HPLC analysis of bis-MTPA ester G derived from F. 

The symposium and book would not have been possible without the financial assistance of Ajinomoto Company, Inc. Hasegawa Company, Ltd. Kirin Brewery Company, Ltd. Ogawa Company, Ltd. and Takasago International Corporation. We are grateful for their generous contributions. 

Research and cloning of ATFl was carried out in collaboration with Ozeki Co., Ltd. 1 wish to express sincere thanks to Mr. Masaaki Hamachi and his colleagues at Ozeki Research Laboratories for their cooperation in this research and I would like to thank Dr. Reisuke Takahashi of KIRIN Brewery Co., Ltd. for permission to publish this work. I would also like to express my appreciation to Dr. Hiroyuki Yoshimoto for valuable discussion, and Miss Keiko Kanai and Mrs. Ritsuko Katoh for technical assistance. 

In Japan, continuous production processes using immobilized living cells are currently introduced in such classical areas as beer (Kirin Brewery Co.) and sake brewing (Ohzeki, Co. Ltd), vinegar production (Kewpie Jyozo, Co. Ltd), and in the production of soy sauce (Kik-koman Co.). 

Kirin Brewery Co., Ltd, Japan (1985) The anthracycline compound AG-2 and its antitumor activity. Jpn Kokai Tokkyo Koho JP Patent 60025 999 (Chem Abstr 104 33023)... 

Due to fascinating bioactivities, KRN7000 (2) has continuously attracted organic chemists synthetic interest. After the disclosure of the stmcture 2 by Kirin Brewery [2], many reports on the synthesis of 2 were published [5,7,9]. 

S.R. FERRI, O. ISHIZAKI-NISHIZAWA, M. AZUMA and T. TOGURI Central Laboratories for Key Technology, Kirin Brewery Co., Ltd., Fukuura, Kanazawa, Yokohama 236, Japan... 

Lee and Mukherjee employed the dienyne metathesis protocol for the synthesis of the C1-C19 fragment of (—)-cochleamycin A (246, Scheme 24.59), which was isolated by the Kirin Brewery group from Streptomy-ces sp. to exhibit antitumor and antimicrobial activities The metathesis precursor 242 was prepared by stepwise reactions of trialkynylsilane 240 with alcohols 239 and 241. Exposure of 242 to [Ru]-II forms bicyclic siloxane 243, and removal of the silicon tether by TBAF afforded E,Z-1,3-dienediol 244 in 61% yield. The subsequent manipulations to 245 were carried out effectively. 

---