公开(公告)号：JPH03264547A

公开(公告)日：1991-11-25

申请号：JP6185290

申请日：1990-03-13

Applicant: AGENCY IND SCIENCE TECHN

Inventor： NAMIKAWA HIROYUKI ,  NAKANISHI FUSAE ,  HADO MASAKATSU

IPC: B01J23/44 ,  C07B61/00 ,  C07C67/297 ,  C07C69/28

Abstract: PURPOSE:To produce the subject long chain acyl derivatives of tartaric acid of high purity useful as a surfactant, etc., and capable of ready separation in a high yield by passing through a long chain acyl derivative of dibenzyl tartarate as an intermediate of synthesis. CONSTITUTION:A long chain acyl derivative of dibenzyl tartarate [e.g. dibenzyl (2R, 3R)-ditetradecanoyl tartarate] represented by formula I (R is 7-17C long chain alkyl) is synthesized as a synthetic intermediate and then subjected to hydrogenation decomposition to obtain the objective long chain alkyl derivative of tartaric acid [e.g. (2R,3R)-ditetradecanoyl tartaric acid] expressed by formula II. The above-mentioned synthetic intermediate of formula I is obtained by reacting dibenzyl tartarate with a long chain carboxylic acid chloride in the presence of pyridine and 4-dimethylaminopyridine. The finally synthesized compound is a surfactant having hydrophilic groups in combination with hydrophobic groups in one molecule.

公开(公告)号：JPH02282351A

公开(公告)日：1990-11-19

申请号：JP10294989

申请日：1989-04-21

Applicant: AGENCY IND SCIENCE TECHN

Inventor： NAMIKAWA HIROYUKI ,  SHIMIZU TOSHIMI ,  HADO MASAKATSU

IPC: C07C213/02 ,  C07C215/40

Abstract: NEW MATERIAL:The compound of formula I (X is halogen; n is 10-20). EXAMPLE:16-Hydroxyhexadecyldimethyloctadecyl ammonium bromide. USE:Useful as an emulsifier, stabilizer, dispersing agent and wetting agent for foods, cosmetics, dyes, etc., or as a surface-modifying material for fiber, plastics, metal, ceramics, glass, etc. It is useful also as a drug carrier material, organic thin film material, etc. PREPARATION:The objective compound of formula l can be produced by mixing and heating a long-chain halo-alcohol of formula II with a compound of formula III in a solvent such as ethanol.

公开(公告)号：JPH09140380A

公开(公告)日：1997-06-03

申请号：JP30138895

申请日：1995-11-20

Applicant: AGENCY IND SCIENCE TECHN

Inventor： BABA TERUHIKO ,  NAMIKAWA HIROYUKI ,  HADO MASAKATSU ,  MOTOKI AKIHIRO ,  HIRANO MASAHIKO

IPC: G01N33/545 ,  C07K17/02 ,  C12N11/08

Abstract: PROBLEM TO BE SOLVED: To provide the subject substrate capable of immobilizing a membrane protein useful in a bioreactor engineering field, etc., to enable activity control of the protein by blending a specific glucolipid with an anionic lipid as components. SOLUTION: A synthetic glucolipid represented by the formula [R is an 12-18C straight-chain saturated alkyl or a straight-chain unsaturated alkyl or phytanyl; (n) is an integer of 1-7] is mixed with an anionic lipid (e.g. sulfoquinobosyl diglyceride) as components to prepare a lipid membrane substrate for immobilizing membrane protein and the protein is dissolved in chloroform into 10mol% concentration and the solvent is distilled away from the solution to prepare the phospholipid thin film and subjected to vacuum drying one night and a buffer aqueous solution is added thereto to prepare a multilamellar vesicle and filtered using a filter having 0.1μm pores under nitrogen gas pressure to afford a single membrane vesicle and the membrane protein is immobilized to provide the objective lipid membrane.

公开(公告)号：JPH0680618A

公开(公告)日：1994-03-22

申请号：JP26085992

申请日：1992-09-03

Applicant: AGENCY IND SCIENCE TECHN

Inventor： SHIMIZU TOSHIMI ,  NAMIKAWA HIROYUKI ,  MURAKAMI TEIICHI ,  HADO MASAKATSU

IPC: C07C233/47 ,  C07C237/22

Abstract: PURPOSE:To obtain a new long chain alkyl derivative of an amino acid, useful as a synthetic intermediate for surfactants or amphiphatic substances capable of forming an organic thin film or a closed type liposome in water and functioning as an emulsifying agent in a two-component system or water and an oil and having high reactivity. CONSTITUTION:The objective long-chain alkyl derivative of an amino acid is expressed by the formula (X is hydroxymethyl or carboxyl; Y is O constituting an ester or NH constituting an amide; R and R' are 12-18C long-chain alkyl), e.g. N-tetradecanoyl-L-serine-dodecyl ester. This compound expressed by the formula is obtained by reacting serine having protected amino and hydroxyl groups with a long-chain alkylamine or a long-chain alkyl alcohol, then removing the protecting groups, reacting a long-chain fatty acid therewith and finally releasing the protecting group of hydroxyl group. Since this compound expressed by the formula already contains the long-chain alkyl as a hydrophobic group in its structure, hydrophilic residues can be coupled to a chemical substance ranging from a low to a high polymers to simply afford a wide range of functional surfactants and amphiphatic substances.

公开(公告)号：JPH03264569A

公开(公告)日：1991-11-25

申请号：JP6185190

申请日：1990-03-13

Applicant: AGENCY IND SCIENCE TECHN

Inventor： NAMIKAWA HIROYUKI ,  MURAKAMI TEIICHI ,  HADO MASAKATSU

IPC: C07D263/24 ,  C07D498/04

Abstract: NEW MATERIAL:2N,3O-Carbonyl-D-threosphingosine shown by formula V. USE:Capable of directly introducing hydrophilic part of sphingolipid, useful as an intermediate for synthesizing sphingolipid forming microsome (ribosome) of underwater closing type and having physiologically activity such as cytostatic action, an intermediate for synthesizing an emulsifying agent, stabilizing agent and wetting gent of food, cosmetic, dye, etc., an intermediate for synthesizing a material for drug carrier for packing water soluble drugs into microsome or an intermediate for surface modifying material of matter adaptable to organisms. material. PREPARATION:D-Glucosamine hydrochloride shown by formula I is reacted with phenyl chloroformate to give a compound shown by formula II, which is treated with a strongly basic ion exchange resin to give a compound shown by formula III. This compound is subjected to reduction reaction with a reducing agent and to cleavage reaction with a cleaving agent to give a compound shown by formula IV, which is finally olefinized to give a compound shown by formula V.

公开(公告)号：JP2000344797A

公开(公告)日：2000-12-12

申请号：JP15264199

申请日：1999-05-31

Applicant: AGENCY IND SCIENCE TECHN

Inventor： BABA TERUHIKO ,  NAMIKAWA HIROYUKI ,  HADO MASAKATSU ,  MOTOKI AKIHIRO ,  HIRANO MASAHIKO

IPC: B01F17/42 ,  B01F17/56 ,  C07K14/405 ,  C07K14/415

Abstract: PROBLEM TO BE SOLVED: To provide a method for industrially advantageously producing a lipid vesicle membrane incorporated with a photosynthetic membrane protein, having no restriction on concentration of a surfactant used, capable of increasing the incorporation efficiency of the protein in spite of simple treatment operation and highly maintaining the water-splitting activity ability of photochemical system II protein aggregate. SOLUTION: In this method for producing a lipid vesicle membrane incorporated with a photosynthetic membrane protein by incorporating a photosynthetic membrane protein into a lipid vesicle membrane in the presence of a surfactant, an osmotic substance such as preferably glycinebetaine is further added to the production. Moreover, the osmotic substance is glycine betaine and a photosynthetic membrane protein is a photochemical system II protein aggregate. A lipid constituting a vesicle membrane is not particularly restricted if the lipid is in a liquid crystal state in a dialysis temperature condition. A natural phospholipid, natural glycolipid, synthetic phospholipid, synthetic glycolipid, a synthetic amphiphatic substance having vesicle membrane forming properties, etc., may be cited as the lipid.

公开(公告)号：JPH11123096A

公开(公告)日：1999-05-11

申请号：JP18872998

申请日：1998-07-03

Applicant: AGENCY IND SCIENCE TECHN

Inventor： BABA TERUHIKO ,  NAMIKAWA HIROYUKI ,  HADO MASAKATSU ,  MOTOKI AKIHIRO ,  HIRANO MASAHIKO

IPC: C12P3/00 ,  A61K9/127 ,  C07K14/405 ,  C07K14/415 ,  C08L5/00 ,  C08L89/00

Abstract: PROBLEM TO BE SOLVED: To obtain a photosynthetic membrane protein-integrated vesicle membrane, which does not cause any low-temperature trouble, can be used at a wide range of temperature, retains proton and the like within the vesicle in a closed state for a long time, has stable tolerance to electric potential difference generated by proton gradient and the like, and is useful to utilize ion gradient separated by a membrane, wherein a lipid layer is a vesicle membrane. SOLUTION: The photosynthetic membrane protein-integrated vesicle membrane, which a photosynthetic membrane protein is integrated in a vesicle membrane comprising a 1,3-bisphytanylglycerylether-type oligosaccharide glycolipid and an anionic lipid, is obtained by adding a surfactant to a vesicle membrane comprising a 1,3-bisphytanylglycerylether-type oligosaccharide glycolipid and an anionic lipid at such a concentration of the surfactant that the vesicle membrane is not solubilized even partially but only swollen, then adding a photosynthetic membrane protein, followed by removal of the surfactant.

公开(公告)号：JPH08245682A

公开(公告)日：1996-09-24

申请号：JP5281195

申请日：1995-03-13

Applicant: AGENCY IND SCIENCE TECHN

Inventor： NAMIKAWA HIROYUKI ,  HADO MASAKATSU

IPC: C07H15/04 ,  B01F17/42 ,  B01F17/56

Abstract: PURPOSE: To obtain the subject new glycolipid as a specific 1,3- bisphytanylgliceryl ether-type oligosaccharide glycolipid and having excellent chemical stability and hydration swelling ability, and useful for dispersant, humectant, a material for drug carrier and a biocompatible material, etc. CONSTITUTION: The objective new 1,3-bisphytanylgliceryl ether-type oligosaccharide glycolipid is expressed by formula I ((n) is an integer of >=1). The compound is useful as a cosmetic, a food, a dispersant such as a dye, an emulsifier, a stabilizer, a solubilizer, a humectant and a penetrant or as a material for a drug carrier keeping a water-soluble drug in a microcapsule, and further, as a biocompatible material an organic film material, a raw material of an organic substrate relating to semiconductor and a surface modifier of fibers, plastic, metal and ceramic, etc. The compound is obtained by reacting phytanyl alcohol of formula II with epichlorohydrine in the presence of a salt to obtain 1,3-bisphytanylgliceryl ether and reacting with maltoligosaccharide α-trichloroacetoimidate.

公开(公告)号：JPH07258178A

公开(公告)日：1995-10-09

申请号：JP7408594

申请日：1994-03-18

Applicant: AGENCY IND SCIENCE TECHN

Inventor： MURAKAMI TEIICHI ,  NAMIKAWA HIROYUKI ,  HADO MASAKATSU

IPC: C07D319/06 ,  B01J27/135 ,  C07B61/00 ,  C07C213/02 ,  C07C215/24 ,  C07D263/14 ,  C07D319/20 ,  C07D413/06

Abstract: PURPOSE:To obtain the compound from inexpensively and readily obtainable starting raw materials by reacting N-benzoyl-D-glucosamine with an acetalizing agent, then reducing, sulfonylating, deacetalizing, iodizing and treating with a base. CONSTITUTION:N-Benzoyl-D-glucosamine is reacted with an acetalizing agent to give a 4,6-acetal of the formula I (Bz is benzoyl R is a 1-4C alkyl or phenyl; R is H, a 1-4C alkyl, etc.). The compound is reduced to obtain a 2-benzamido-2- deoxy-D-glucitol derivative. The derivative is simultaneously sulfonylated and made into an oxanoline derivative to obtain a phenyloxazoline derivative of the formula II (Ph is phenyl; R is a 1-4C acetal or an aryl), which is acetalized, the iodized and simultaneously eliminated reductively to give an end vinyl compound of the formula III. The compound is treated with a base, the prepared epoxide is reacted with a dodecyl Grignard reagent in the presence of a curpous salt, the oxanoline ring is cleft and the benzonyl group is eliminated to obtain the compound of the formula IV (R to R each is H).

公开(公告)号：JPH0680685A

公开(公告)日：1994-03-22

申请号：JP26085892

申请日：1992-09-03

Applicant: AGENCY IND SCIENCE TECHN

Inventor： SHIMIZU TOSHIMI ,  NAMIKAWA HIROYUKI ,  MURAKAMI TEIICHI ,  HADO MASAKATSU

IPC: A61K9/127 ,  B01F17/56 ,  B01J13/02 ,  C07H15/04 ,  C09K19/06

Abstract: PURPOSE:To provide the subject new compound useful as a material for organic thin films or liposome, having amphiphaticity comparable to those of natural analogues, also high in the thermal stability of the films therefrom in the form of solid phase, significantly highly pure compared to natural analogues, and capable of mass production from inexpensive materials. CONSTITUTION:The objective compound of formula I (S is aldose residue with the reduced terminal carbon involved in o-glycoside linkage; R and R' are each 12-18C alkyl), e.g. N-tetradecanoyl-o-(beta-D-glucopyranoside)-L-serine-dodecyl ester. The compound of the formula I can be obtained by reaction of a serine long chain alkyl derivative of formula II with 1 to 3 molar times of a reduced terminal-activated sugar chain component of formula Z-Y (Z is aldose residue with all of the hydroxyl groups except the reduced terminal one protected by acetyl groups; Y is active group for the o-glycoside linkage formation at the reduced terminal) to form an o-glycoside linkage followed by eliminating the acetyl groups as the protecting groups for the sugar chain components.