Eisai Company, Limited

Agency of Industrial Science and Technology

General Director of the Agency of Industrial Science and Technology

Director-general of the Agency of Industrial Science and Technology

Ministry of International Trade & Industry

Agency of Industrial Science and Technology Ministry of International

Mitsubishi Precision Co., Ltd.

Hokkaido Sugar Co., Ltd.

Esai Co., Ltd.

Yoshimasa Takahara

Shizumasa Kijima

Kenji Nakajima

Akio Sato

Shinya Abe

Kouzi Yamada

Noriaki Kuwana

Yoshiyuki Takasaki

Isao Yamatsu

Takeshi Suzuki

Yuichi Inai

Ryuichiro Kurane

Hideaki Watanabe

Tomio Tsurugi

Yoshiyuki Kawakami

Kouichi Suzuki

Chikashi Izumi

Tamio Kawamura

Masaru Yamada

Tomoo Suzuki

Masahiko Nishiguchi

Yoshiyuki Kohara

Toshihiko Nakamura

Toshiharu Kumazawa

Atsushi Mori

Norio Futai

Atsuhi Mori

Toshio Murakami

There are disclosed polyprenyl sulfone derivatives of the general formula: ##STR1## wherein n represents an integer of 1-4, R.sub.1 represents an aryl group d R.sub.2 represents a hydroxymethyl or carboxyl group. The polyprenyl sulfone derivatives are prepared by cultivating a microorganism of the genus Nocardia capable of oxidizing a compound of the general formula: ##STR2## wherein n and R.sub.1 have the same meanings as defined above, in a culture medium containing a compound of the above general formula (II), and then collecting the oxidation product from the culture mixture. The polyprenyl sulfone derivatives are useful as intermediates for preparing various useful polyprenyl compounds.

Polyprenyl sulfone derivatives and process for producing the same

A liquid starch solution suitable for saccharification into a maltose-containing product is obtained by suspending starch in water, adding to the starch suspension a heat resistant .alpha.-amylase and a carbonate, adjusting the resultant mixture to a pH value in the range of from 7.5 to 8.0, and thermally treating the resultant starch milk while repressing possible hydrolysis of starch molecules.

Process for liquefaction of starch

Polyprenyl carboxylic acid derivatives having the general formula (I): ##STR1## in which n is an integer of from 2 to 4, R.sub.1 represents the hydrogen atom or a protecting group for the carboxylic acid group, and R.sub.2 represents a hydroxymethyl, formyl or carboxyl group, are disclosed. A process for the preparation of the polyprenyl carboxylic acid derivative involving microbiological oxidation using a strain belonging to the genus Nocardia is disclosed. The compounds have anti-ulcer activity and hypotensive activity. The compounds also are useful as intermediates for preparing polyprenyl carboxylic acids of the formula ##STR2## and esters thereof, wherein l is an integer of from 4 to 11. The polyprenyl carboxylic acids and esters thereof have hypotensive activity and anti-ulcer activity.

Polyprenyl carboxylic acid derivatives

A process is disclosed for the preparation of a compound having the general formula: ##STR1## wherein n is an integer of from 2 to 4, R.sub.1 is an ester-forming moiety effective as a protecting group for a carboxyl group, and R.sub.2 is hydroxymethyl, formyl or carboxyl. The compounds (I) are useful as intermediates for the preparation of polyprenyl compounds having hypotensive and anti-ulcer activity. The process of the invention includes cultivating a microorganism selected from a strain of the genus Nocardia called BPM 1613, FERM-P No. 1609, Corynebacterium equi IAM 1038, Candida lipolytica IFO 0746, and Mycobacterium smegmatis IFO 3083, in a nutritive culture medium, in the presence of a compound having the general formula: ##STR2## wherein R.sub.3 is an ester-forming moiety effective as a protecting group for a carboxyl group, whereby the microorganism utilizes the compound (II) as a carbon source and oxidizes the compound (II), thereby converting the compound (II) into the compound (I).

Process for preparing polyprenyl carboxylic acid derivatives

Longer carbon chain polyprenyl ketone derivatives are prepared by cultivag Nocardia strain FERM-P No. 1609 in the presence of shorter carbon chain polyprenyl ketones.

Process for the preparation of polyprenyl ketone derivatives

A process for the preparation of a two-functional-group-containing terpenoid having the general formula: ##STR1## in which n is an integer of from 1 to 5, R represents a hydroxymethyl, formyl or carboxyl group, and A represents the hydrogen atom, or a 2-tetrahydropyranyl, benzyl, methoxymethol or methoxyethoxymethyl group comprising the oxidation with a microorganism belonging to the genus Nocardia. Some of the terpenoids are of value as anti-ulcer agents, while others are useful as intermediates.

Two-functional-group-containing terpenoids, processes for the

This invention relates to novel polyprenyl ketone derivatives having the eral formula: ##STR1## in which n is an integer of 1-5, and R represents a hydroxymethyl, formyl or carboxyl group, and a process for the preparation of the same.

Polyprenyl ketone derivatives

Polyprenyl sulfones

Anti-ulcer composition comprising terpenoid containing two functional

A liquid starch solution suitable for saccharification into a maltose-containing product is obtained by suspending starch in water, adding to the starch suspension a heat resistant .alpha.-amylase and a buffer, adjusting the resultant mixture to a pH value in the range of from 7.5 to 8.0, and thermally treating the resultant starch milk while repressing possible hydrolysis of starch molecules.

A process for the preparation of a two-functional-group-containing terpen having the general formula: ##STR1## in which n is an integer of from 1 to 5, R represents a hydroxymethyl, formyl, or carboxyl group, and A represents the hydrogen atom, or a 2-tetrahydropyranyl, benzyl, methoxymethol or methoxyethoxymethyl group comprising the oxidation with a microorganism belonging to the genus Nocardia. Some of the terpenoids are of value as anti-ulcer agents, while others are useful as intermediates.

Two-functional-group-containing terpenoids

A vessel capable of passing a liquid therethrough is packed with a support having at least hydrophilicity and microorganism cells are inoculated to the support, retained and cultivated therein. A reaction substrate is fed to the vessel and brought into contact with the microorganism, whereby the microorganism is allowed to propagate within the support and act upon the reaction substrate to induce decomposition or synthetic reactions thereof.

Biochemical treatment by microorganic method

Microorganisms of a species selected from the group consisting of the specific species belonging to genus Nocardia, genus Pseudomonas, genus Brevibacterium and genus Corynebacterium, when cultured in a culture medium containing a phthalic acid ester as a carbon source, assimilate the phthalic acid ester and decompose it into carbon dioxide gas and water.

Method for decomposition of phthalic acid esters by use of microorganisms

Growing community of inventors

Narashino, Japan

Yoshimasa Takahara