JPH0331718B2 - - Google Patents
Info
- Publication number
- JPH0331718B2 JPH0331718B2 JP58073959A JP7395983A JPH0331718B2 JP H0331718 B2 JPH0331718 B2 JP H0331718B2 JP 58073959 A JP58073959 A JP 58073959A JP 7395983 A JP7395983 A JP 7395983A JP H0331718 B2 JPH0331718 B2 JP H0331718B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- integer
- methacrylate
- range
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 150000003904 phospholipids Chemical class 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000012528 membrane Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 230000007910 cell fusion Effects 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- -1 N,N-di-iso - propylaminoethyl Chemical group 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940042880 natural phospholipid Drugs 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- NMGPHUOPSWFUEB-UHFFFAOYSA-N 2-(butylamino)ethyl 2-methylprop-2-enoate Chemical compound CCCCNCCOC(=O)C(C)=C NMGPHUOPSWFUEB-UHFFFAOYSA-N 0.000 description 1
- UATUCIKYJLUTBD-UHFFFAOYSA-N 2-(dibutylamino)ethyl 2-methylprop-2-enoate Chemical compound CCCCN(CCCC)CCOC(=O)C(C)=C UATUCIKYJLUTBD-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- KZUIKPMQAIEBOE-UHFFFAOYSA-N 2-(ethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCNCCOC(=O)C(C)=C KZUIKPMQAIEBOE-UHFFFAOYSA-N 0.000 description 1
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 description 1
- 229940061334 2-phenylphenol Drugs 0.000 description 1
- SNCMCDMEYCLVBO-UHFFFAOYSA-N 3-aminopropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCN SNCMCDMEYCLVBO-UHFFFAOYSA-N 0.000 description 1
- AOIUPKVEPBMRDZ-UHFFFAOYSA-N 4-aminobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCN AOIUPKVEPBMRDZ-UHFFFAOYSA-N 0.000 description 1
- UKLKEQPYSNOCNO-UHFFFAOYSA-N 6-aminohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCN UKLKEQPYSNOCNO-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- GSMQGKBIUJXJPK-UHFFFAOYSA-N methylamino 2-methylprop-2-enoate Chemical compound CNOC(=O)C(C)=C GSMQGKBIUJXJPK-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- External Artificial Organs (AREA)
- Materials For Medical Uses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
本発明はリン脂質類似構造を有する化合物の製
造方法に関するものである。
（従来技術）
生体内には多種のリン脂質が含まれており、こ
れらのリン脂質は生体が生命を維持するために重
要な役割を演じていることが明らかにされてい
る。
例えば、リン脂質は細胞膜等の細胞質の構成要
素であり、生体の種々な代謝過程と密接な関係が
あり、又その他、脳組織のエネルギー源、脂肪の
運搬及び吸収、血液の凝固、食物の味の知覚等に
も非常に重要な役割を演じている。
このように、リン脂質は全体の生命維持におい
て多くの機能をもつため、各種の人工臓器、細胞
融合、酵素の固定、人工栽培、バイオセンサー等
へ応用しようとする試みが数多くなされている。
しかし一般にこれらの試みに用いられているリ
ン脂質はレシチン、ホスフアチジルエタノールア
ミン、ホスフアチジルセリン等いずれも生体から
抽出した天然物であり、低分子量であるため、均
一で強固な膜を得ることは著しく困難である。
そこで上述した湿度センサ、ガスセンサ、イオ
ン透視膜、人工臓器、細胞融合、酵素の固定、バ
イオセンサ、人工栽培等の分野に利用するために
は、これらが比較的高分子のもので得られ、かつ
強固に製膜化し得ること、及びこれらが経済性の
高いことなどに関する要請が著しく高い状況にあ
る。
（発明の目的）
本発明の目的はこれらの要請に応ずることので
きるリン脂質類似構成の化合物を効率良く製造し
得る方法を提供しようとするものである。
（発明の構成）
即ち、本発明は、
一般式
及び一般式
（式中Ｒは
The present invention relates to a method for producing a compound having a phospholipid-like structure. (Prior Art) It has been revealed that living organisms contain many types of phospholipids, and these phospholipids play an important role in maintaining the life of living organisms. For example, phospholipids are components of cytoplasm such as cell membranes, and are closely related to various metabolic processes in living organisms.They are also an energy source for brain tissue, transport and absorption of fat, coagulation of blood, and the taste of food. It also plays a very important role in perception. Since phospholipids have many functions in supporting overall life, many attempts have been made to apply them to various artificial organs, cell fusion, enzyme immobilization, artificial cultivation, biosensors, etc. However, the phospholipids generally used in these attempts, such as lecithin, phosphatidylethanolamine, and phosphatidylserine, are all natural products extracted from living organisms and have low molecular weights, making it difficult to obtain uniform and strong membranes. This is extremely difficult. Therefore, in order to be used in the above-mentioned fields such as humidity sensors, gas sensors, ion-permeable membranes, artificial organs, cell fusion, enzyme immobilization, biosensors, and artificial cultivation, it is necessary to obtain these materials with relatively high molecular weight and There is an extremely high demand for these materials to be able to be formed into strong films and to be highly economical. (Objective of the Invention) An object of the present invention is to provide a method for efficiently producing a compound having a structure similar to that of a phospholipid, which can meet these demands. (Structure of the invention) That is, the present invention has the general formula and general formula (In the formula, R is
【式】【formula】
【式】−CnH2n+1、R′及びR″はそれぞれ
−Ｈ、−CpH2p+1よりなる群から選択された置換
基を表わし、ｍは２〜12の範囲の整数、ｐは１〜
４の範囲の整数を表わす）
で表わされる化合物を溶媒中で反応させることを
特徴とする一般式、
で表わされるリン脂質類似構造を有する化合物の
製造方法である。
以下本発明を詳細に説明する。
（発明の構成及び実施例）
先づ例えば文献（Makromol.Chem.，Rapid
Commum.3，457−459（1982）あるいはPolymer
Preprints，Japan，page、2735〜2738，vol.31，
No.10）に記載された方法に従い、次式(4)(5)の如く
２−クロロ−１，３，２−ジオキシホスホラン
（）を合成した。
生成した化合物（）とｐ−フエニルフエノール
を用い、同文献に記載された方法に従い、次式(6)
の如く２フエニルフエノキシ−２−オキソ−１，
３，２−ジオキサホスホラン（化合物）を合成
した。
上述の２−フエニルフエノールの代りにフエノ
ール、ｎ−ドデシルアルコール、ｎ−ヘキシルア
ルコール、ｎ−ブチルアルコール、ｎ−プロピル
アルコール、又はエチルアルコールを用いて反応
させ、次の一般式による化合物（）を合成し
た。
（式中Ｒは[Formula] -C n H 2n+1 , R' and R'' each represent a substituent selected from the group consisting of -H and -C p H 2p+1 , m is an integer in the range of 2 to 12, p is 1~
(representing an integer in the range of 4) is reacted in a solvent, This is a method for producing a compound having a phospholipid-like structure represented by The present invention will be explained in detail below. (Structure and Examples of the Invention) First, for example, literature (Makromol.Chem., Rapid
Commum.3, 457-459 (1982) or Polymer
Preprints, Japan, page, 2735-2738, vol.31,
According to the method described in No. 10), 2-chloro-1,3,2-dioxyphosphorane () was synthesized as shown in the following formulas (4) and (5). Using the generated compound () and p-phenylphenol, according to the method described in the same document, the following formula (6)
2-phenylphenoxy-2-oxo-1,
3,2-dioxaphosphorane (compound) was synthesized. A reaction is performed using phenol, n-dodecyl alcohol, n-hexyl alcohol, n-butyl alcohol, n-propyl alcohol, or ethyl alcohol in place of the above-mentioned 2-phenylphenol to obtain a compound () according to the following general formula. Synthesized. (In the formula, R is
【式】【formula】
【式】−CnH2n+1であり、又ｍは２〜12
の範囲の整数を表わす）。
次に上述した化合物（）0.1モル及びＮ，Ｎ
−ジメチルアミノエチルメタクリレート（CH2＝
Ｃ（CH3）CO2（CH2）2N（CH3）2）0.1モルを300cm3
のアセトニトリルに溶解し、耐圧びんに入れ50〜
60℃で振蕩させながら30時間反応させた。反応終
了後溶液中のアセトニトリルを減圧溜去した後、
残留物を大過剰のアセトン中に投入し、静置後上
澄液を捨て残渣を採取した。同様の操作を３回繰
返した後残渣を真空乾燥し更にこの乾燥残渣をメ
チルアルコールに溶解後脱脂綿を用いて過し、
液を大過剰のアセトン中に撹拌しながら滴下
し、静置後上澄液を捨てた。同様の操作を２〜３
回繰返し得られた生成物を真空乾燥した後秤量し
たところ、収率は約75％であつた。この生成物の
元素分及び赤外線吸収分析の結果は次表１の通り
であり、これらの分析結果から該生成物は次の如
き式(7)の反応によつて生成した２−〔２−（メタク
リロイルオキシ）エチルジメチルアンモニウム〕
エチル−ｐ−ジフエニルホスフエート（化合物
）であることが確認された。[Formula] -C n H 2n+1 , and m represents an integer in the range of 2 to 12). Next, 0.1 mol of the above compound () and N,N
-dimethylaminoethyl methacrylate (CH 2 =
C( CH3 ) CO2 ( CH2 ) 2N ( CH3 ) 2 ) 0.1 mol in 300cm3
Dissolve in acetonitrile and place in a pressure bottle for 50~
The reaction was allowed to proceed for 30 hours while shaking at 60°C. After the reaction is complete, acetonitrile in the solution is distilled off under reduced pressure,
The residue was poured into a large excess of acetone, left to stand, the supernatant was discarded, and the residue was collected. After repeating the same operation three times, the residue was vacuum dried, and the dried residue was dissolved in methyl alcohol and filtered through absorbent cotton.
The solution was added dropwise to a large excess of acetone with stirring, and after standing still, the supernatant was discarded. 2-3 similar operations
When the product obtained repeatedly was vacuum dried and weighed, the yield was about 75%. The elemental content and infrared absorption analysis results of this product are shown in Table 1 below. From these analysis results, the product is 2-[2-( methacryloyloxy)ethyldimethylammonium]
It was confirmed to be ethyl-p-diphenyl phosphate (compound).
上述のアセトニトリルの代りに、ジメチルホル
ムアミド（DMF）又はメチルアルコールを溶媒
として反応させた場合、収率に若干の差異はある
が前記の場合と同様の化合物（）が得られた。
次に上記の各種のアルコールを用いて合成した
化合物（）のいずれか１種の上記Ｎ，Ｎ−ジメ
チルアミノエチルメタクリレートを用いて上記と
同様に反応させ精製した。得られた反応生成物の
元素分析及び赤外線吸収分析の結果は次表２の通
りであり、これらの分析結果から生成物は化合物
（）と類似の構造をもつ次式(8)の化合物（）
であることが確認された。
次に、Ｎ，Ｎ−ジメチルアミノエチルメタクリ
レートの代りにＮ，Ｎ−ジエチルアミノエチルメ
タクリレート（CH2＝Ｃ（CH3）CO2（CH2）2N
（C2H5）2）、Ｎ，Ｎ−ジ−iso−プロピルアミノエ
チルタクリレート（CH2＝Ｃ（CH3）CO2
（CH2）2N〔CH（CH3）2〕2）、Ｎ，Ｎ−ジ−ｎ−ブチ
ルアミノエチルメタクリレート（CH2＝Ｃ（CH3）
CO2（CH2）Ｎ〔（CH2）3CH3〕2）、Ｎ−メチルアミ
ノメタクリレート（CH2＝Ｃ（CH3）CO2
（CH2）2NH（CH3））、Ｎ−エチルアミノエチルメ
タクリレート（CH2＝Ｃ（CH3）CO2（CH2）2NH
（C2H5））、Ｎ−ｎ−ブチルアミノエチルメタクリ
レート（CH2＝Ｃ（CH3）CO2（CH2）2NH
（CH2）3CH3）、２−アミノエチルメタクリレート
（CH2＝Ｃ（CH3）CO2（CH2）2N（H2）、３−アミ
ノ−１−プロピルメタクリレート（CH2＝Ｃ
（CH3）CO2（CH2）2NH2）、４−アミノ−１−ブ
チルメタクリレート（CH2＝Ｃ（CH3）CO2
（CH2）2NH2）、６−アミノ−１−ヘキシルメタク
リレート（CH2＝Ｃ（CH3）CO2（CH2）6NH2）の
いずれか１種と、上記２フエニルフェノキシ−２
−オキソ−１，３，２−ジオキサホスホラン（化
合物）を(7)式と同様に反応させ精製した。得ら
れた反応生成物の元素分析及び赤外線吸収分析の
結果は次表３の通りであり、これらの分析結果か
ら生成物は化合物（）と類似の構造をもつ次式
(9)の化合物（）であることが確認された。
以上の実施例より、化合物（）及び化合物
（）を後記(10)式のように反応させると化合物
（）を生成することが明らかになつた。
本発明の化合物はメタクロイル基
When dimethylformamide (DMF) or methyl alcohol was used as a solvent instead of acetonitrile, the same compound () as in the above case was obtained, although the yield was slightly different. Next, using the N,N-dimethylaminoethyl methacrylate of any one of the compounds () synthesized using the various alcohols mentioned above, the mixture was reacted and purified in the same manner as above. The results of elemental analysis and infrared absorption analysis of the obtained reaction product are shown in Table 2 below, and from these analysis results, the product is a compound () of the following formula (8) having a similar structure to compound ().
It was confirmed that Next, N,N-diethylaminoethyl methacrylate (CH2 = C( CH3) CO2( CH2 ) 2N ) was substituted for N,N-dimethylaminoethyl methacrylate.
( C2H5 ) 2 ), N,N-di-iso - propylaminoethyl tacrylate ( CH2 =C( CH3 ) CO2
( CH2 ) 2N [CH( CH3 ) 2 ] 2 ), N,N-di-n-butylaminoethyl methacrylate ( CH2 =C( CH3 )
CO 2 (CH 2 )N [(CH 2 ) 3 CH 3 ] 2 ), N-methylamino methacrylate (CH 2 =C(CH 3 )CO 2
( CH2 ) 2NH ( CH3 )), N-ethylaminoethyl methacrylate ( CH2 =C( CH3 ) CO2 ( CH2 ) 2NH
( C2H5 )), N-n-butylaminoethyl methacrylate ( CH2 =C( CH3 ) CO2 ( CH2 ) 2NH
( CH2 ) 3CH3 ), 2-aminoethyl methacrylate ( CH2 =C( CH3 ) CO2 ( CH2 ) 2N ( H2 ), 3 - amino-1-propyl methacrylate ( CH2 =C
( CH3 ) CO2 ( CH2 ) 2NH2 ), 4-amino - 1-butyl methacrylate ( CH2 =C( CH3 ) CO2
(CH 2 ) 2 NH 2 ), 6-amino-1-hexyl methacrylate (CH 2 =C(CH 3 )CO 2 (CH 2 ) 6 NH 2 ), and the above 2 phenylphenoxy-2
-Oxo-1,3,2-dioxaphosphorane (compound) was reacted and purified in the same manner as in formula (7). The results of elemental analysis and infrared absorption analysis of the obtained reaction product are shown in Table 3 below, and from these analysis results, the product has the following formula with a similar structure to compound ().
It was confirmed that it was the compound () of (9). From the above examples, it was revealed that compound () is produced when compound () and compound () are reacted as shown in formula (10) below. The compound of the present invention has a methacryloyl group.
【式】を有しているため、通常の
ラジカル重合法で容易にその重合体を得ることが
できる。
（但し式中R′及びR″は−Ｈ、−CnH2n+1、ｍは
２〜12、ｎは２〜６の範囲の整数を表わす）
（式中ｎは２〜６の範囲の整数、Ｒは
Since it has the formula, the polymer can be easily obtained by ordinary radical polymerization methods. (However, in the formula, R' and R'' represent -H, -C n H 2n+1 , m represents an integer in the range of 2 to 12, and n represents an integer in the range of 2 to 6.) (In the formula, n is an integer in the range of 2 to 6, R is
【式】−Cn
H2n+1、R′及びR″はそれぞれ−Ｈ、−CpH2p+1より
なる群から選択された置換基を表わし、ｍは２〜
12の範囲の整数、ｐは１〜４の範囲の整数を表わ
す。）[Formula] -C n H 2n+1 , R' and R'' each represent a substituent selected from the group consisting of -H and -C p H 2p+1 , m is 2 to
an integer in the range of 12; p represents an integer in the range of 1 to 4; )
【表】【table】
【表】【table】
【表】
（発明の効果）
以上の説明から明らかなように、本発明によれ
ば特にリン脂質構成のポリマーを、前式にて示さ
れる如き前駆体とも考えられる中間体を経ること
によりわずかの反応工程で簡単に、かつ高収率及
び反応性の高い状態で合成でき工業的規模で経済
性良く安価に製造し得る。
そして本発明による上記リン脂質類似構造を有
する化合物からなるポリマーは従来の天然リン脂
質にはみられない性質を有し、すなわちポリマー
であることから膜の形成が極めて容易であり、か
つ得られた膜は天然のリン脂質に比べはるかに強
固なものとなる。従つて上述した湿度センサ、ガ
スセンサ、イオン透過膜、人工臓器、細胞融合、
酵素の固定、バイオセンサ、人工栽培等の広い分
野への利用が可能となりその工業的価値は非常に
大きい。[Table] (Effects of the Invention) As is clear from the above explanation, according to the present invention, a polymer having a phospholipid structure can be produced by passing through an intermediate, which can also be considered as a precursor, as shown in the previous formula. It can be easily synthesized in a reaction process with high yield and high reactivity, and can be produced economically and inexpensively on an industrial scale. The polymer made of the compound having a structure similar to phospholipids according to the present invention has properties not found in conventional natural phospholipids; in other words, since it is a polymer, it is extremely easy to form a membrane, and The membrane is much stronger than natural phospholipids. Therefore, the above-mentioned humidity sensors, gas sensors, ion permeable membranes, artificial organs, cell fusion,
It can be used in a wide range of fields such as enzyme immobilization, biosensors, and artificial cultivation, and its industrial value is extremely large.
Claims (1)
基を表わし、ｍは２〜12の範囲の整数、ｐは１〜
４の範囲の整数を表わす） で表わされる化合物を溶媒中で反応させることを
特徴とする一般式、 で表わされるリン脂質類似構造を有する化合物の
製造方法。[Claims] 1. General formula and general formula (In the formula, R is [Formula] [Formula] -C n H 2n+1 , R' and R'' each represent a substituent selected from the group consisting of -H and -C p H 2p+1 , and m is An integer in the range of 2 to 12, p is 1 to
(representing an integer in the range of 4) is reacted in a solvent, A method for producing a compound having a phospholipid-like structure represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58073959A JPS59199696A (en) | 1983-04-28 | 1983-04-28 | Compound having lipid-like structure and polymer and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58073959A JPS59199696A (en) | 1983-04-28 | 1983-04-28 | Compound having lipid-like structure and polymer and their preparation |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12255987A Division JPS6386704A (en) | 1987-05-21 | 1987-05-21 | Polymer from compound having phospholipid-like structure |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59199696A JPS59199696A (en) | 1984-11-12 |
| JPH0331718B2 true JPH0331718B2 (en) | 1991-05-08 |
Family
ID=13533124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58073959A Granted JPS59199696A (en) | 1983-04-28 | 1983-04-28 | Compound having lipid-like structure and polymer and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59199696A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2144062A1 (en) | 2008-05-15 | 2010-01-13 | Biocompatibles UK Limited | Method of monitoring live cells |
| EP2267049A1 (en) | 2003-02-05 | 2010-12-29 | Biocompatibles UK Limited | Block copolymers |
| WO2012175923A1 (en) | 2011-06-24 | 2012-12-27 | Biointeractions Limited, University Of Reading | Biocompatible, biomimetic ampholyte materials |
| WO2020003147A2 (en) | 2018-06-29 | 2020-01-02 | Biocompatibles Uk Limited | Radiopaque polymers |
| WO2020003152A2 (en) | 2018-06-29 | 2020-01-02 | Biocompatibles Uk Limited | Biodegradable polymer |
| US10874611B2 (en) | 2016-02-25 | 2020-12-29 | Ucl Business Ltd | Chemotactic, drug-containing polymersomes |
| US10881613B2 (en) | 2016-03-17 | 2021-01-05 | Ucl Business Ltd | Fumarate polymersomes |
| EP4066902A4 (en) * | 2019-11-29 | 2023-12-20 | Tokushima University | Zwitterion compound and production method and use for same |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8835541B2 (en) | 2005-09-14 | 2014-09-16 | Daihachi Chemical Industry Co., Ltd. | Phosphorus compounds, use thereof and flame retarding polyester fibers |
| US9533006B2 (en) | 2007-11-19 | 2017-01-03 | University Of Washington | Marine coatings |
| CA2705485C (en) * | 2007-11-19 | 2016-03-08 | University Of Washington | Cationic betaine precursors to zwitterionic betaines having controlled biological properties |
| WO2011057224A2 (en) | 2009-11-06 | 2011-05-12 | University Of Washington Through Its Center For Commercialization | Zwitterionic polymer bioconjugates and related methods |
-
1983
- 1983-04-28 JP JP58073959A patent/JPS59199696A/en active Granted
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2267049A1 (en) | 2003-02-05 | 2010-12-29 | Biocompatibles UK Limited | Block copolymers |
| EP2144062A1 (en) | 2008-05-15 | 2010-01-13 | Biocompatibles UK Limited | Method of monitoring live cells |
| WO2012175923A1 (en) | 2011-06-24 | 2012-12-27 | Biointeractions Limited, University Of Reading | Biocompatible, biomimetic ampholyte materials |
| US10874611B2 (en) | 2016-02-25 | 2020-12-29 | Ucl Business Ltd | Chemotactic, drug-containing polymersomes |
| US10881613B2 (en) | 2016-03-17 | 2021-01-05 | Ucl Business Ltd | Fumarate polymersomes |
| WO2020003147A2 (en) | 2018-06-29 | 2020-01-02 | Biocompatibles Uk Limited | Radiopaque polymers |
| WO2020003152A2 (en) | 2018-06-29 | 2020-01-02 | Biocompatibles Uk Limited | Biodegradable polymer |
| EP4130105A1 (en) | 2018-06-29 | 2023-02-08 | Biocompatibles UK Limited | Biodegradable polymer |
| EP4066902A4 (en) * | 2019-11-29 | 2023-12-20 | Tokushima University | Zwitterion compound and production method and use for same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59199696A (en) | 1984-11-12 |
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