JPS6118544B2 - - Google Patents
Info
- Publication number
- JPS6118544B2 JPS6118544B2 JP2051178A JP2051178A JPS6118544B2 JP S6118544 B2 JPS6118544 B2 JP S6118544B2 JP 2051178 A JP2051178 A JP 2051178A JP 2051178 A JP2051178 A JP 2051178A JP S6118544 B2 JPS6118544 B2 JP S6118544B2
- Authority
- JP
- Japan
- Prior art keywords
- polyamine
- spermine
- fraction
- acid
- nmr
- 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
Links
- 229920000768 polyamine Polymers 0.000 claims description 16
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 14
- 229940063675 spermine Drugs 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 230000001737 promoting effect Effects 0.000 description 3
- 238000001243 protein synthesis Methods 0.000 description 3
- 230000014616 translation Effects 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- RMRCNWBMXRMIRW-BYFNXCQMSA-M cyanocobalamin Chemical compound N#C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O RMRCNWBMXRMIRW-BYFNXCQMSA-M 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 230000006819 RNA synthesis Effects 0.000 description 1
- 241000868182 Thermus thermophilus HB8 Species 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 229960002104 cyanocobalamin Drugs 0.000 description 1
- 235000000639 cyanocobalamin Nutrition 0.000 description 1
- 239000011666 cyanocobalamin Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229960005010 orotic acid Drugs 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 229940063673 spermidine Drugs 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明はポリアミンに関する。更に詳しくは高
度好熱性細菌サーマスサーモフイラス（Termus
thermophilus）HB8から得られた新規ポリアミン
に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to polyamines. For more information, see the highly thermophilic bacterium Termus thermophilus.
thermophilus) HB8.
近年来、プトレツシン、スペルミン、スペルミ
ジンのようなポリアミン類の生物学における重要
性が注目されており、その生物活性が明らかにさ
れつつある。ポリアミン類は細胞の増殖などの生
命現象の基幹的作用に関与しており、蛋白合成の
促進、酵素の保譲作用、酵素の活性化、RNA合
成促進、膜の安定化など多岐にわたり重要な役割
を果している。 In recent years, the importance of polyamines such as putrescine, spermine, and spermidine in biology has attracted attention, and their biological activities are being clarified. Polyamines are involved in fundamental functions of life phenomena such as cell proliferation, and play a variety of important roles such as promoting protein synthesis, preserving enzymes, activating enzymes, promoting RNA synthesis, and stabilizing membranes. is fulfilled.
本発明者等は、ポリアミン類の生命現象におけ
る重要な役割に注目し、新規ポリアミンの調製を
試みた結果、本発明を達成した。 The present inventors have focused on the important role of polyamines in biological phenomena, attempted to prepare a new polyamine, and have achieved the present invention.
本発明の要旨は、
式NH2（CH2）3NH（CH2）3NH（CH2）4NH2で表わ
されるポリアミンに存する。 The gist of the invention consists in polyamines of the formula NH 2 (CH 2 ) 3 NH (CH 2 ) 3 NH (CH 2 ) 4 NH 2 .
本発明のポリアミンは、高度好熱性細菌サーマ
スサーモフイラス（Termus thermophilus）
HB8（ATCC27634）の菌体から採取される採取
法は、先ず菌体を破砕し、10％トリクロル酢酸を
加え遠心し、その上清をDowex50×4H+樹脂
〔Dowchemical社製イオン交換樹脂（商標）〕カラ
ムにかけ、H2O〜6NHCの線状濃度勾配で溶出
し、HC濃度3.7N〜4.8Nにテトラアミンの分画
を得、これをダイヤイオンCK−10S〔三菱化成
社の強酸性陽イオン交換樹脂、ダイヤイオンは登
録商標〕カラムにかけ、PH5.46の緩衝液で溶出
すれば、テルミンの分画のすぐ後に、本発明のポ
リアミンの分画が得られる。 The polyamine of the present invention is produced by the highly thermophilic bacterium Termus thermophilus.
The method for collecting HB8 (ATCC27634) cells is to first crush the cells, add 10% trichloroacetic acid, centrifuge, and transfer the supernatant to Dowex 50 x 4H + resin (ion exchange resin (trademark) manufactured by Dowchemical). ] Column and eluted with a linear concentration gradient of H 2 O to 6NHC to obtain a fraction of tetraamine at an HC concentration of 3.7N to 4.8N, which was collected using Diaion CK-10S [Mitsubishi Kasei Corporation's strongly acidic cation exchange If the resin, Diamond Ion is a registered trademark, is applied to a column and eluted with a pH 5.46 buffer, the polyamine fraction of the present invention will be obtained immediately after the theremin fraction.
この分画を集め、脱塩、再結晶をしてのち、プ
ロトン−NMR、13C−NMR、赤外線吸収スペク
トル、質量分折等により、このポリアミンが式
NH2（CH2）3NH（CH2）3NH（CH2）4NH2を有する
新規ポリアミンであることが同定される。 After collecting these fractions, desalting and recrystallizing them, proton-NMR, 13 C-NMR, infrared absorption spectra, mass spectrometry, etc. were used to determine whether this polyamine had a formula.
A novel polyamine is identified having NH 2 (CH 2 ) 3 NH (CH 2 ) 3 NH (CH 2 ) 4 NH 2 .
本発明のポリアミンは、デオキシリボ酸の熱変
性に対する保護、蛋白質合成の促進、スペルミン
の蛋白質合成促進効果に対する阻害、酵素の活性
化等種々の興味深い生理作用を有し、医薬として
の用途が考えられる。 The polyamine of the present invention has various interesting physiological actions, such as protection against thermal denaturation of deoxyriboic acid, promotion of protein synthesis, inhibition of the protein synthesis promoting effect of spermine, and activation of enzymes, and can be used as a medicine.
実施例 １
高度好熱性細菌サーマスサーモフイラスHB8
（ATCC27634）を0.5％ペプトン、0.4％酵母エキ
ス、0.2％塩化ナトリウム、0.1％グリコール及び
0.05％無機塩ビタミン溶液（水１中に25gMgC
２・6H2O、5gCaC２、2gMnSO4・6H2O、
0.5gZnSO4・7H2O、0.5gH3BO3、5gFeC３・
6H2O、15mgCuSO425mgNa2MoO4・2H2O、50mg
CoNO3・6H2O、20mgNiNO3・6H2O80mgピリドキ
サン、10mg葉酸、0.5mlH2SO4、10mgチアミン・
ピロリン酸、40mgリボフラビン、80mgニコチンア
ミド、80mgパラアミノ安息香酸、10mgビオチン、
0.4mgシアノコバラミン、80mgパントテイン酸、
20mgリポン酸、200mgイノシトール、50mgオロチ
ン酸、100mgスペルミンを含む）を含む培地を用
いて75℃で培養した。Example 1 Highly thermophilic bacterium Thermus thermophilus HB8
(ATCC27634) 0.5% peptone, 0.4% yeast extract, 0.2% sodium chloride, 0.1% glycol and
0.05% inorganic salt vitamin solution (25gMgC in 1 part water)
2.6H 2 O, 5gCaC 2 , 2gMnSO 4.6H 2 O,
0.5gZnSO 4・7H 2 O, 0.5gH 3 BO 3 , 5gFeC 3・
6H2O , 15mgCuSO4 25mgNa2MoO4 ・ 2H2O , 50mg
CoNO 3 6H 2 O, 20 mg NiNO 3 6H 2 O 80 mg pyridoxane, 10 mg folic acid, 0.5 ml H 2 SO 4 , 10 mg thiamine.
Pyrophosphate, 40mg riboflavin, 80mg nicotinamide, 80mg para-aminobenzoic acid, 10mg biotin,
0.4mg cyanocobalamin, 80mg pantotheic acid,
The cells were cultured at 75°C using a medium containing 20 mg liponic acid, 200 mg inositol, 50 mg orotic acid, and 100 mg spermine.
後記対数増殖期で集菌した菌体湿重量150gを
水150mlに懸濁し音波処理により菌体を破砕し
た。10％トリクロ酢酸150mlを加え、遠心し、そ
の上清をDowex50×4H+樹脂〔Dowchemical社製
イオン交換樹脂（商標）〕カラムにかけた。10ml
H2O、次いで50ml0.1Mリン酸ナトリウム緩衝液
PH8.0（0.7MNaCを含む）、更に20mlH2Oでそ
れぞれカラムを洗浄後、H2O（１）〜6NHC
（１）の線状濃度勾配で溶出した。溶出液の一
部をとりニンヒドリン発色させると、HC濃度
3.2N〜3.7Nにトリアミンの分画、3.7N〜4.8Nに
テトラアミンの分画が得られていることがわかつ
た。 A wet weight of 150 g of bacterial cells collected in the logarithmic growth phase described below was suspended in 150 ml of water, and the bacterial cells were disrupted by sonication. 150 ml of 10% trichloroacetic acid was added, centrifuged, and the supernatant was applied to a Dowex 50×4H + resin (ion exchange resin (trademark) manufactured by Dowchemical) column. 10ml
H2O then 50ml 0.1M sodium phosphate buffer
After washing the column with PH8.0 (containing 0.7M NaC) and 20 ml H 2 O, add H 2 O (1) to 6 NHC.
Elution was performed using a linear concentration gradient (1). When a portion of the eluate is taken and colored with ninhydrin, the HC concentration is determined.
It was found that a triamine fraction was obtained between 3.2N and 3.7N, and a tetraamine fraction was obtained between 3.7N and 4.8N.
テトラアミン分画を集めエバポレーターで濃縮
乾固し、水を加え再乾固し、残査を３〜４mlの
H2Oに溶かした。次いでこれをダイヤイオンCK
−10S〔三菱化成社の強塩基性陰イオン交換樹
脂、ダイヤイオンには登録商標をつめたカラムに
加え、緩衝液（クエン酸カリ37.75g、KC
149g、4NHC10〜11mlにH2Oを加え１にし、
PHを5.64に調整したもの）を0.84ml／minで流
し、1.5min／tubeで分画した。tube number140
〜175にテルミンの分画が得られ、その後の175〜
240の分画に新規ポリアミンの分画が得られた。
このうち185〜230の分画をとり、次の方法により
脱塩した。 The tetraamine fractions were collected and concentrated to dryness using an evaporator, and water was added and dried again.
Dissolved in H2O . Next, add this to Diaion CK
-10S [Mitsubishi Kasei Corporation's strongly basic anion exchange resin, Diaion is a registered trademark of the column packed with buffer solution (potassium citrate 37.75 g, KC
Add H2O to 149g, 10-11ml of 4NHC to make 1,
(pH adjusted to 5.64) was flowed at 0.84 ml/min and fractionated at 1.5 min/tube. tube number 140
A fraction of theremin was obtained at ~175 and then at ~175
A novel polyamine fraction was obtained in 240 fractions.
Of these, 185 to 230 fractions were taken and desalted using the following method.
すなわち、Dowex50×4H+樹脂〔Dowchemical
社製イオン交換樹脂（商標）〕のカラムに加え、
1NHC50mlで洗浄、6NHCで溶出した。１
ml／tubeの割合で分画した。tubenumber5〜10を
集め、減圧乾固し、再び水を加えて減圧乾固し
た。 That is, Dowex50×4H + resin〔Dowchemical
In addition to a column of ion exchange resin (trademark) made by
Washed with 50 ml of 1NHC and eluted with 6NHC. 1
It was fractionated at the ratio of ml/tube. Tube numbers 5 to 10 were collected, dried under reduced pressure, water was added again, and dried under reduced pressure.
残査を約0.1ml位の水に溶解し、エタノール：
メタノール＝１：１の混液15mlを加え、−20℃で
放置した。沈澱を遠心で集め、エタノールで洗浄
し、65℃で乾燥した。収量は60mgであつた。 Dissolve the residue in about 0.1ml of water and add ethanol:
15 ml of a 1:1 mixture of methanol was added, and the mixture was allowed to stand at -20°C. The precipitate was collected by centrifugation, washed with ethanol, and dried at 65°C. The yield was 60 mg.
得られたポリアミンについては、スペルミンを
対照試料として、赤外線吸収スペクトル、プロト
ン−NMR及びマススペクトルを測定した。 Regarding the obtained polyamine, infrared absorption spectrum, proton-NMR, and mass spectrum were measured using spermine as a control sample.
赤外線吸収スペクトルにより、得られたポリア
ミンはスペルミンと異なる物質であることが判明
した。プロトン−NMRでは、Ｎが４個あるこ
と、炭素についている水素が全部で20個であり、
そして該水素は3.1PPM、2.1PPMおよび1.8PPM
の３つのピークに大別され、それぞれａ，ｂ，ｃ
とおくと、積分比でａ：ｂ：ｃ＝３：１：１であ
り、スペルミンとの比較により、ａがＮのすぐ隣
りのｃについている水素、ｂがプロピレン基の真
中のｃの水素、ｃがブチレン基の２位、３位のｃ
の水素であることから、プロキレン基を２個有
し、ブチレン基を１個有することが判明した。ま
たマススペクトルから、分子量が202であること
分解物のピークとして分子量144のピークがあり
（スペルミンには、このピークがなく、分子量158
のピークがある）、この分解物は−CH2NH
（CH2）3NH（CH2）3NH2であることがわかつた。 Infrared absorption spectroscopy revealed that the obtained polyamine was a substance different from spermine. In proton-NMR, there are 4 N atoms and a total of 20 hydrogen atoms attached to carbon.
And the hydrogen is 3.1PPM, 2.1PPM and 1.8PPM
It is roughly divided into three peaks, a, b, and c, respectively.
Then, the integral ratio is a:b:c=3:1:1, and by comparison with spermine, a is the hydrogen attached to c immediately next to N, b is the hydrogen attached to c in the middle of the propylene group, c is at the 2nd and 3rd positions of the butylene group
Since it is hydrogen, it was found that it has two prokylene groups and one butylene group. Also, from the mass spectrum, the molecular weight is 202, and there is a peak with a molecular weight of 144 as a peak of the decomposed product (spermine does not have this peak, and has a molecular weight of 158
), this decomposition product is −CH 2 NH
It turned out to be (CH 2 ) 3 NH (CH 2 ) 3 NH 2 .
以上のように、ここで得られたポリアミンは、
主として赤外線吸収スペクトル、プロトンNMR
及びマススペクトルのデータから、更に13C−
NMRなどのデータから、式NH2（CH2）3NH
（CH2）3NH（CH2）4NH2を有する化合物であるこ
とが同定された。 As mentioned above, the polyamine obtained here is
Mainly infrared absorption spectrum, proton NMR
Furthermore, from the mass spectrum data, 13 C−
From data such as NMR, the formula NH 2 (CH 2 ) 3 NH
It was identified as a compound having (CH 2 ) 3 NH(CH 2 ) 4 NH 2 .
Claims (1)
表わされるポリアミン。1 A polyamine represented by the formula NH 2 (CH 2 ) 3 NH (CH 2 ) 3 NH (CH 2 ) 4 NH 2 .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2051178A JPS55302A (en) | 1978-02-24 | 1978-02-24 | Polyamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2051178A JPS55302A (en) | 1978-02-24 | 1978-02-24 | Polyamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55302A JPS55302A (en) | 1980-01-05 |
| JPS6118544B2 true JPS6118544B2 (en) | 1986-05-13 |
Family
ID=12029174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2051178A Granted JPS55302A (en) | 1978-02-24 | 1978-02-24 | Polyamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55302A (en) |
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| WO2021085637A1 (en) | 2019-10-31 | 2021-05-06 | キヤノン株式会社 | Cell culture method, method for producing culture solution, culture solution and culture device |
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|---|---|---|---|---|
| CN114525230B (en) * | 2022-03-31 | 2024-04-09 | 杭州优玛达生物科技有限公司 | Fermentation culture and fermentation method of thermophilic thermus strain using fermentation culture |
-
1978
- 1978-02-24 JP JP2051178A patent/JPS55302A/en active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200036900A (en) | 2017-08-31 | 2020-04-07 | 캐논 가부시끼가이샤 | Method for producing ultra-fine air bubbles, apparatus and method for manufacturing ultra-fine air bubble-containing liquid, and ultra-fine air bubble-containing liquid |
| EP3703467A1 (en) | 2019-02-28 | 2020-09-02 | Canon Kabushiki Kaisha | Ultrafine bubble generating apparatus |
| EP3702332A1 (en) | 2019-02-28 | 2020-09-02 | Canon Kabushiki Kaisha | Ultrafine bubble generating method, ultrafine bubble generating apparatus, and ultrafine bubble-containing liquid |
| EP3702022A1 (en) | 2019-02-28 | 2020-09-02 | Canon Kabushiki Kaisha | Ultrafine bubble generating method, ultrafine bubble generating apparatus, and ultrafine bubble-containing liquid |
| EP3702331A1 (en) | 2019-02-28 | 2020-09-02 | Canon Kabushiki Kaisha | Ultrafine bubble generating method, ultrafine bubble generating apparatus, and ultrafine bubble-containing liquid |
| WO2021085637A1 (en) | 2019-10-31 | 2021-05-06 | キヤノン株式会社 | Cell culture method, method for producing culture solution, culture solution and culture device |
| WO2021085629A1 (en) | 2019-10-31 | 2021-05-06 | キヤノン株式会社 | Method for producing ultra-fine bubble-containing liquid, ultra-fine bubble-containing liquid, method for utilizing ultra-fine bubbles, and device for utilizing ultra-fine bubbles |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55302A (en) | 1980-01-05 |
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