JP2585079B2 - New dipeptide compounds - Google Patents
New dipeptide compoundsInfo
- Publication number
- JP2585079B2 JP2585079B2 JP63260239A JP26023988A JP2585079B2 JP 2585079 B2 JP2585079 B2 JP 2585079B2 JP 63260239 A JP63260239 A JP 63260239A JP 26023988 A JP26023988 A JP 26023988A JP 2585079 B2 JP2585079 B2 JP 2585079B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- group
- obzl
- gaba
- glu
- 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
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は植物生長調整作用を有する新規ジペプチド化
合物に関する。Description: TECHNICAL FIELD The present invention relates to a novel dipeptide compound having a plant growth regulating action.
（従来の技術） 近年、食料問題の深刻化が予想されており、農産物の
生産量の確保、さらには増産に向けての努力が必要とさ
れ、多くの研究が行われている。本発明者らは、異常気
象等による農産物の減産を最小限に留めることも重要で
あると考え、例えば、低温環境にさらされた農作物に対
し、その生長力の正常化作用を有する化合物を探索して
きた。その結果、本発明者らは本発明ジペプチド化合物
に植物生長調整作用のあることを見出し、本発明を完成
した。(Prior Art) In recent years, the seriousness of the food problem is expected, and efforts are needed to secure the production of agricultural products and further increase the production, and many studies are being conducted. The present inventors consider that it is also important to minimize the decrease in production of agricultural products due to abnormal weather and the like, and, for example, search for a compound having a normalizing effect on the growth potential of crops exposed to a low-temperature environment. I've been. As a result, the present inventors have found that the dipeptide compound of the present invention has a plant growth regulating action, and have completed the present invention.
（発明が解決しようとする問題点） 本発明の目的は、植物生長調整作用を有する新規ジペ
プチド化合物及び該化合物を有効成分として含有する農
園芸用剤を提供することにある。(Problems to be Solved by the Invention) An object of the present invention is to provide a novel dipeptide compound having a plant growth regulating action and an agricultural and horticultural agent containing the compound as an active ingredient.
（問題点を解決するための手段） 本発明ジペプチドは、下記一般式（Ｉ）で表される新
規化合物である。(Means for Solving the Problems) The dipeptide of the present invention is a novel compound represented by the following general formula (I).
〔式中、Ｒは水素又はアミノ基の保護基、Ｙは水素又は
保護基を有してもよい水酸基、Ｘは１以上の保護基を有
してもよい酸性アミノ酸残基を表す。〕 本発明においては、ペプチド及びアミノ酸は国際純正
応用化学連合（IUPAC）−国際生化学連合（IUB）採用の
略号及び当該分野で繁用されている略号で表され、例え
ば下記の略号が使用される。 [Wherein, R represents a hydrogen or amino protecting group, Y represents a hydrogen or a hydroxyl group optionally having a protecting group, and X represents an acidic amino acid residue optionally having one or more protecting groups. In the present invention, peptides and amino acids are represented by abbreviations adopted by the International Union of Pure and Applied Chemistry (IUPAC) -International Union of Biochemistry (IUB) and abbreviations commonly used in the art. For example, the following abbreviations are used. You.
GABA:γ−アミノ酪酸 GABOB:β−ヒドロキシ−γ−アミノ酪酸 Glu:グルタミン酸 Asp:アスパラギン酸 前記一般式（Ｉ）中、ＸはGlu、Ｄ−Glu、Asp、Ｄ−A
sp等の酸性アミノ酸残基を表し、該アミノ酸残基は１以
上の保護基を有してもよい。例えば好ましい化合物とし
て、GABA−Glu、GABA−Ｄ−Glu、GABA−Asp、GABA−Ｄ
−Asp、GABOB−Glu、GABOB−Ｄ−Glu、GABOB−Asp、GAB
OB−Ｄ−Asp等が挙げられる。GABA: γ-aminobutyric acid GABOB: β-hydroxy-γ-aminobutyric acid Glu: glutamic acid Asp: aspartic acid In the general formula (I), X is Glu, D-Glu, Asp, DA
represents an acidic amino acid residue such as sp, and the amino acid residue may have one or more protecting groups. For example, preferred compounds include GABA-Glu, GABA-D-Glu, GABA-Asp, GABA-D
-Asp, GABOB-Glu, GABOB-D-Glu, GABOB-Asp, GAB
OB-D-Asp and the like.
本発明ジペプチド化合物は、ペプチド化学における通
常の方法によって製造することができる。即ち、本発明
ジペプチド化合物の合成は、液相法でも固相法でも可能
である。The dipeptide compound of the present invention can be produced by a usual method in peptide chemistry. That is, the dipeptide compound of the present invention can be synthesized by a liquid phase method or a solid phase method.
ペプチド結合を形成させるための縮合法としては、ア
ジド法、活性エステル法、混合酸無水物法、酸クロリド
法、酵素的縮合法、N,N′−ジシクロヘキシルカルボジ
イミド（DCC）、水溶性カルボジイミド、N,N′−カルボ
ニルジイミダゾール等の縮合剤を用いる方法、或いはDC
Cと共にＮ−ヒドロキシスクシンイミド、Ｎ−ヒドロキ
シ−５−ノルボルネン−2,3−ジカルボキシイミド、１
−ヒドロキシベンゾトリアゾール等の添加剤を使用する
DCC−添加剤法など通常のペプチド縮合法を利用するこ
とができる。Condensation methods for forming peptide bonds include azide method, active ester method, mixed acid anhydride method, acid chloride method, enzymatic condensation method, N, N'-dicyclohexylcarbodiimide (DCC), water-soluble carbodiimide, N Using a condensing agent such as N, N'-carbonyldiimidazole, or DC
C together with N-hydroxysuccinimide, N-hydroxy-5-norbornene-2,3-dicarboximide,
-Use additives such as hydroxybenzotriazole
Usual peptide condensation methods such as the DCC-additive method can be used.
縮合反応に際して原料となるアミノ酸は、通常用いら
れる保護基を有しているものを用いることができ、反応
に関与しないアミノ基及び側鎖官能基を公知の方法で保
護したり、また反応に関与するカルボキシル基、アミノ
基を活性化させてもよい。As the amino acid used as a raw material in the condensation reaction, those having a commonly used protecting group can be used, and the amino group and side chain functional group not involved in the reaction can be protected by a known method, or can be used in the reaction. Carboxyl group and amino group may be activated.
反応に関与しないアミノ基の保護基としては、通常の
ペプチド合成で用いられる保護基が利用でき、即ち、ｔ
−ブトキシカルボニル、ｔ−ペントキシカルボニル等の
低級アルコキシカルボニル基、ベンジルオキシカルボニ
ル等のアラルキルオキシカルボニル基又はｏ−クロロベ
ンジルオキシカルボニル、ｐ−ニトロベンジルオキシカ
ルボニル、ｐ−メトキシベンジルオキシカルボニル等の
置換基を有するアラルキルオキシカルボニル基などが挙
げられる。As the protecting group for the amino group which does not participate in the reaction, a protecting group used in ordinary peptide synthesis can be used.
-Butoxycarbonyl, lower alkoxycarbonyl groups such as t-pentoxycarbonyl, aralkyloxycarbonyl groups such as benzyloxycarbonyl or substituents such as o-chlorobenzyloxycarbonyl, p-nitrobenzyloxycarbonyl, p-methoxybenzyloxycarbonyl, etc. And an aralkyloxycarbonyl group having the formula:
グルタミン酸、アスパラギン酸などの酸性アミノ酸残
基のカルボキシル基の保護基としては、通常のペプチド
合成で用いられるカルボキシル基の保護基、即ち、ベン
ジルオキシ等のアラルキルオキシ基、ｐ−メトキシベン
ジルオキシ等の置換基を有するアラルキルオキシ基、ｔ
−ブトキシ、ｔ−ペントキシ等の低級アルコキシ基、シ
クロペンチルオキシ、シクロヘキシルオキシ等のシクロ
アルキルオキシ基若しくは４−ピリジロキシ基などが利
用できる。As a protecting group for a carboxyl group of an acidic amino acid residue such as glutamic acid or aspartic acid, a protecting group for a carboxyl group used in ordinary peptide synthesis, that is, substitution of an aralkyloxy group such as benzyloxy or p-methoxybenzyloxy. An aralkyloxy group having a group, t
Lower alkoxy groups such as -butoxy and t-pentoxy, cycloalkyloxy groups such as cyclopentyloxy and cyclohexyloxy, and 4-pyridyloxy groups can be used.
また、β−ヒドロキシ−γ−アミノ酪酸の水酸基の保
護基としては、通常のペプチド合成で用いられる水酸基
の保護基が利用でき、即ち、ベンジル等のアラルキル
基、ブロモベンジル、クロロベンジル等の置換基を有す
るアラルキル基、ｔ−ブチル等の低級アルキル基などが
挙げられる。Further, as the hydroxyl-protecting group of β-hydroxy-γ-aminobutyric acid, a hydroxyl-protecting group used in ordinary peptide synthesis can be used, that is, an aralkyl group such as benzyl and a substituent such as bromobenzyl and chlorobenzyl. And a lower alkyl group such as t-butyl and the like.
これらの置換基は、接触還元、酸分解等の通常の手段
により除去することができる。These substituents can be removed by usual means such as catalytic reduction and acid decomposition.
縮合反応及び脱保護基反応における反応温度、時間、
溶媒等は、通常のペプチド合成で用いられる反応条件に
従って設定することができる。Reaction temperature, time, in condensation reaction and deprotection group reaction,
The solvent and the like can be set according to the reaction conditions used in ordinary peptide synthesis.
本発明ジペプチド化合物はその薬学的に許容される塩
を包含し、例えば無機塩としてナトリウム、カリウム等
のアルカリ金属、カルシウム、バリウム等のアルカリ土
類金属、その他のアルミニウム等の金属との塩、或いは
アンモニウム等との有機アミンとの塩などが挙げられ
る。The dipeptide compound of the present invention includes pharmaceutically acceptable salts thereof, for example, as an inorganic salt, an alkali metal such as sodium, potassium, calcium, an alkaline earth metal such as barium, a salt with another metal such as aluminum, or Examples thereof include salts with organic amines such as ammonium.
又、本発明化合物はその金属錯化合物を包含し、例え
ば亜鉛、ニッケル、コバルト、銅、鉄等との錯化合物が
挙げられる。Further, the compound of the present invention includes its metal complex compound, for example, a complex compound with zinc, nickel, cobalt, copper, iron and the like.
これらの塩並びに金属錯化合物は公知の方法により遊
離の本発明ジペプチドより製造でき、或いは相互に変換
することができる。These salts and metal complex compounds can be produced from the free dipeptide of the present invention by known methods, or can be mutually converted.
本発明におけるアミノ酸残基はＤ−体、Ｌ−体、DL−
体の何れであってもよい。The amino acid residues in the present invention are D-form, L-form, DL-
It can be any of the body.
得られた本発明化合物は、クロマトグラフィー、再結
晶等の通常の手段により精製し、元素分析、融点、NM
R、IR、UV、マススペクトル等により同定を行った。
尚、比旋光度はナトリウムのＤ線を用いて測定した。The obtained compound of the present invention is purified by ordinary means such as chromatography and recrystallization, and is subjected to elemental analysis, melting point, NM
Identification was performed by R, IR, UV, mass spectrum and the like.
The specific rotation was measured using the D line of sodium.
以下に、本発明製造方法の一例を実施例により説明す
る。Hereinafter, an example of the manufacturing method of the present invention will be described with reference to an example.
尚、以下の実施例においては、置換基及び試薬等の略
号として次のものを用いる。In the following examples, the following are used as abbreviations for substituents and reagents.
Z:ベンジルオキシカルボニル OBzl:ベンジルオキシ TosOH:トルエンスルホン酸 EDC.HCl:1−エチル−３−（３′−ジメチルアミノプロ
ピル）−カルボジイミド塩酸塩 （実施例） 実施例1. （１）5.36gのトリエチルアミン、11.9gのＺ−GABA−OH
及び26.5gのTosOH・Glu（OBzl）−OBzlを塩化メチレン2
50mlに溶かし、氷冷下にて53mmolのEDC.HClを加え、０
℃で２時間、室温で20時間かき混ぜた。溶媒を減圧下に
溜去した後、残渣を酢酸エチル−水に溶かし、有機層を
分離した。水層を酢酸エチルで抽出した後、有機層を合
わせて、10％クエン酸水溶液、水、５％炭酸水素ナトリ
ウム水溶液、飽和食塩水で順次洗浄した。無水硫酸ナト
リウム上で乾燥した後、溶媒を減圧下に溜去して、白色
結晶を得た。これをシリカゲルカラムクロマトグラフィ
ー（酢酸エチル／クロロホルム＝1/1で溶出）で精製し
て、17.4gのＺ−GABA−Glu（OBzl）−OBzlを得た。Z: benzyloxycarbonyl OBzl: benzyloxy TosOH: toluenesulfonic acid EDC.HCl: 1-ethyl-3- (3'-dimethylaminopropyl) -carbodiimide hydrochloride (Example) Example 1. (1) 5.36 g of Triethylamine, 11.9 g Z-GABA-OH
And 26.5 g of TosOH • Glu (OBzl) -OBzl in methylene chloride 2
Dissolve in 50 ml, add 53 mmol EDC.HCl under ice cooling,
The mixture was stirred at 2 ° C. for 2 hours and at room temperature for 20 hours. After evaporating the solvent under reduced pressure, the residue was dissolved in ethyl acetate-water and the organic layer was separated. After the aqueous layer was extracted with ethyl acetate, the organic layers were combined and washed sequentially with a 10% aqueous citric acid solution, water, a 5% aqueous sodium hydrogen carbonate solution, and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain white crystals. This was purified by silica gel column chromatography (eluted with ethyl acetate / chloroform = 1/1) to obtain 17.4 g of Z-GABA-Glu (OBzl) -OBzl.
収率:64％ 融点:94−95℃ 〔α〕20:＋1.0（cl,CHCl3） 同様にして以下の化合物を得た。Yield: 64% Melting point: 94-95 ° C [α] 20 : +1.0 (cl, CHCl 3 ) The following compound was obtained in the same manner.
Ｚ−GABA−Ｄ−Glu（OBzl）−OBzl 収率:69％ 融点:92−93℃ 〔α〕20:−1.1（cl,CHCl3） Ｚ−GABA−Asp（OBzl）−OBzl 収率:70％ 融点:105−106℃ 〔α〕20:＋15.4（cl,CHCl3） Ｚ−GABA−Ｄ−Asp（OBzl）−OBzl 収率:70％ 融点:104−106℃ 〔α〕20:−15.9（cl,CHCl3） Ｚ−DL−GABOB−Glu（OBzl）−OBzl 白色粉末状結晶 （２）17.4gのＺ−GABA−Glu（OBzl）−OBzlをメタノー
ル200ml、アセトン50ml及び水10mlの混合溶媒に溶か
し、10％パラジウム−炭素触媒の存在下、常温で常圧水
素雰囲気下にて接触還元を行った。20時間後、原料の消
失を薄層クロマトグラフィーで確認した後、触媒を濾去
した。濾液を減圧下に溜去した後、残渣油状物に水とト
ルエンを加え、酢酸を減圧下に共沸除去した。残渣油状
物をエタノールから結晶化した後、水−エタノールより
再結晶して、白色粉末状の6.6gのGABA−Glu（化合物
１）を得た。Z-GABA-D-Glu (OBzl) -OBzl Yield: 69% Melting point: 92-93 ° C [α] 20 : -1.1 (cl, CHCl 3 ) Z-GABA-Asp (OBzl) -OBzl Yield: 70 % Melting point: 105-106 ° C [α] 20 : +15.4 (cl, CHCl 3 ) Z-GABA-D-Asp (OBzl) -OBzl Yield: 70% Melting point: 104-106 ° C [α] 20 :- 15.9 (cl, CHCl 3 ) Z-DL-GABOB-Glu (OBzl) -OBzl White powdery crystals (2) 17.4 g of Z-GABA-Glu (OBzl) -OBzl mixed with 200 ml of methanol, 50 ml of acetone and 10 ml of water It was dissolved in a solvent and subjected to catalytic reduction in the presence of a 10% palladium-carbon catalyst at room temperature under a hydrogen atmosphere under normal pressure. After 20 hours, the disappearance of the raw materials was confirmed by thin-layer chromatography, and then the catalyst was removed by filtration. After evaporating the filtrate under reduced pressure, water and toluene were added to the residual oil, and acetic acid was removed azeotropically under reduced pressure. The residual oil was crystallized from ethanol and recrystallized from water-ethanol to obtain 6.6 g of GABA-Glu (compound 1) as a white powder.
収率:89％ 融点:178−180℃ 〔ｄ〕20:−4.9（cl,H2O） 元素分析:C9H16N2O5・0.2H2Oとして Ｃ％ Ｈ％ Ｎ％ 計算値： 45.84 7.01 11.88 実測値： 46.02 7.30 11.75 NMR（0.1ND2O,内部標準ｔ−BuOD δ＝1.23）： 1.91−2.02（3H,m）,2.13−2.22（1H,m）,2.42（2H,t,J
＝7.5Hz）,2.46（2H,t,J＝7Hz）,3.02（2H,t,J＝7.5H
z）,4.32（1H,dd,J＝5,9Hz） 同様にして以下の化合物を得た。Yield: 89% mp: 178-180 ° C. [d] 20: -4.9 (cl, H 2 O) Elemental analysis: C 9 H 16 N 2 O 5 · 0.2H C% H% N% Calculated 2 O : 45.84 7.01 11.88 Found: 46.02 7.30 11.75 NMR (0.1ND 2 O, internal standard t-BuOD δ = 1.23): 1.91-2.02 (3H, m), 2.13-2.22 (1H, m), 2.42 (2H, t , J
= 7.5Hz), 2.46 (2H, t, J = 7Hz), 3.02 (2H, t, J = 7.5H)
z), 4.32 (1H, dd, J = 5.9 Hz) The following compounds were obtained in the same manner.
GABA−Ｄ−Glu（化合物２） 収率:86％ 融点:175−176℃ 〔ｄ〕20:＋5.0（cl,H2O） 元素分析:C9H16N2O5・0.2H2Oとして Ｃ％ Ｈ％ Ｎ％ 計算値： 45.84 7.01 11.88 実測値： 45.84 7.11 11.70 NMR（0.1ND2O,内部標準ｔ−BuOD δ＝1.23）： 1.92−2.04（3H,m）,2.15−2.24（1H,m）,2.43（2H,t,J
＝7.5Hz）,2.48（2H,t,J＝7Hz）,3.02（2H,t,J＝7.5H
z）,4.37（1H,dd,J＝5,9Hz） GABA−Asp（化合物３） 収率:92％ 融点:184−185℃ 〔ｄ〕20:＋11.7（cl,H2O） 元素分析:C8H14N2O5として Ｃ％ Ｈ％ Ｎ％ 計算値： 44.03 6.47 12.84 実測値： 44.13 6.79 12.50 NMR（0.1ND2O,内部標準ｔ−BuOD δ＝1.23）： 1.95（2H,tt,J＝7.5,7.5Hz）,2.43（2H,t,J＝7.5Hz）,
2.93（1H,dd,J＝7,17Hz）,2.98（1H,dd,J＝5,17Hz）,3.
01（2H,t,J＝7.5Hz）,4.77（1H,dd,J＝5,7Hz） GABA−Ｄ−Asp（化合物４） 収率:89％ 融点:180−182℃ 〔ｄ〕20:−11.0（cl,H2O） 元素分析:C8H14N2O5として Ｃ％ Ｈ％ Ｎ％ 計算値： 44.03 6.47 12.84 実測値： 43.98 6.67 12.62 NMR（0.1ND2O,内部標準ｔ−BuOD δ＝1.23）： 1.95（2H,tt,J＝7.5,7.5Hz）,2.42（2H,t,J＝7.5Hz）,
2.87（1H,dd,J＝7,17Hz）,2.94（1H,dd,J＝5,17Hz）,3.
10（2H,t,J＝7.5Hz）,4.69（1H,dd,J＝5,7Hz） DL−GABOB−Glu（化合物５） 収率:62％ NMR（0.1ND2O,内部標準ｔ−BuOD δ＝1.23）： 1.95−2.06（1H,m）,2.17−2.26（1H,m）,2.47−2.53
（2H,m）,2.54−2.58（2H,m）,2.96−3.03（1H,m）,3.1
6−3.22（1H,m）,4.23−4.31（1H,m）,4.40−4.46（1H,
m） （作用） 1.植物生長調整作用 ４℃で保存した稲（日本晴）を使用し、本発明化合物
の植物生長調整作用を調べた。GABA-D-Glu (Compound 2) Yield: 86% Melting point: 175-176 ° C [d] 20 : +5.0 (cl, H 2 O) Elemental analysis: C 9 H 16 N 2 O 5 , 0.2 H 2 As O: C% H% N% Calculated: 45.84 7.01 11.88 Found: 45.84 7.11 11.70 NMR (0.1ND 2 O, internal standard t-BuOD δ = 1.23): 1.92−2.04 (3H, m), 2.15−2.24 ( 1H, m), 2.43 (2H, t, J
= 7.5Hz), 2.48 (2H, t, J = 7Hz), 3.02 (2H, t, J = 7.5H)
z), 4.37 (1H, dd, J = 5.9 Hz) GABA-Asp (compound 3) Yield: 92% Melting point: 184-185 ° C [d] 20 : +11.7 (cl, H 2 O) Elemental analysis : C 8 H 14 N 2 O 5 as C% H% N% calculated: 44.03 6.47 12.84 Found: 44.13 6.79 12.50 NMR (0.1ND 2 O, internal standard t-BuOD δ = 1.23): 1.95 (2H, tt , J = 7.5,7.5Hz), 2.43 (2H, t, J = 7.5Hz),
2.93 (1H, dd, J = 7,17Hz), 2.98 (1H, dd, J = 5,17Hz), 3.
01 (2H, t, J = 7.5 Hz), 4.77 (1H, dd, J = 5.7 Hz) GABA-D-Asp (compound 4) Yield: 89% Melting point: 180-182 ° C [d] 20 :- 11.0 (cl, H 2 O) elemental analysis: C 8 H 14 N 2 O 5 as C% H% N% calculated: 44.03 6.47 12.84 Found: 43.98 6.67 12.62 NMR (0.1ND 2 O, internal standard t-BuOD δ = 1.23): 1.95 (2H, tt, J = 7.5,7.5Hz), 2.42 (2H, t, J = 7.5Hz),
2.87 (1H, dd, J = 7,17Hz), 2.94 (1H, dd, J = 5,17Hz), 3.
10 (2H, t, J = 7.5Hz), 4.69 (1H, dd, J = 5,7Hz) DL-GABOB-Glu ( Compound 5) Yield: 62% NMR (0.1ND 2 O , internal standard t-BuOD δ = 1.23): 1.95−2.06 (1H, m), 2.17−2.26 (1H, m), 2.47−2.53
(2H, m), 2.54-2.58 (2H, m), 2.96-3.03 (1H, m), 3.1
6−3.22 (1H, m), 4.23−4.31 (1H, m), 4.40−4.46 (1H, m
m) (Action) 1. Plant growth regulating action Using rice (Nipponbare) stored at 4 ° C, the plant growth regulating action of the compound of the present invention was examined.
被検薬水溶液（１×10-6M）で浸した濾紙をペトリ皿
中に入れて発芽床とし、供試種子を播種した。４日目に
発芽した種子を被検薬水溶液を含まない植物培養試験管
に移して生育試験を行った。移植後７日経過したものの
地上部及び地下部の長さと重量を測定した。一群30個体
とし、試験は20℃の暗所で行い、平均値と標準誤差を求
めた。A filter paper soaked with an aqueous solution of the test drug (1 × 10 −6 M) was placed in a Petri dish to form a germination bed, and test seeds were sown. The seeds germinated on the fourth day were transferred to a plant culture test tube containing no aqueous solution of the test drug, and a growth test was performed. Seven days after the transplantation, the length and weight of the above-ground part and the underground part were measured. The test was performed in a dark place at 20 ° C., and the average value and the standard error were determined.
結果の一例を第１表及び第２表に示す。 Examples of the results are shown in Tables 1 and 2.
（＊＊＊:p＜0.001、＊＊:p＜0.05、＊:p＜0.01） （効果） 以上の結果より明らかなように、本発明化合物は優れ
た植物生長促進作用を有する。この植物生長促進作用
は、低温ストレス下（20℃、稲の最適生長温度は約30
℃）で生長が抑制された植物に対して特に顕著に作用
し、植物生長を正常化する特徴あるものである。(***: p <0.001, **: p <0.05, *: p <0.01) (Effect) As is clear from the above results, the compound of the present invention has an excellent plant growth promoting action. The effect of promoting plant growth is under low-temperature stress (20 ° C, optimal growth temperature of rice is about 30 ° C).
C), which is particularly remarkable for plants whose growth has been suppressed, and has a characteristic of normalizing plant growth.
また、この植物生長正常化作用は、本発明化合物で種
子を発芽期間のみ処理することにより得られるため、非
常に簡便且つ経済的であり、本発明化合物は農園芸用薬
剤等として極めて有用である。Further, since this plant growth normalizing action can be obtained by treating seeds with the compound of the present invention only during the germination period, it is very simple and economical, and the compound of the present invention is extremely useful as an agricultural and horticultural drug and the like. .
───────────────────────────────────────────────────── フロントページの続き (72)発明者 東浦 邦彦 兵庫県加東郡社町木梨字川北山442番１ 日本臓器製薬株式会社生物活性科学研 究所内 (72)発明者 黒橋 正晴 兵庫県加東郡社町木梨字川北山442番１ 日本臓器製薬株式会社生物活性科学研 究所内 (56)参考文献 特開 昭49−127916（ＪＰ，Ａ) ──────────────────────────────────────────────────続 き Continuing on the front page (72) Kunihiko Higashiura Inventor 442-1, Kawakitayama, Kashina-sha, Kato-gun, Hyogo Japan Inside the Institute for Biological Activity Science, Nippon Organ Pharmaceutical Co., Ltd. (72) Masaharu Kurohashi Kato-gun, Hyogo 442-1, Kawakitayama, Shashin-machi, Kinashi-sha Japan Institute of Bioactivity Science, Japan Organ Pharmaceutical Co., Ltd. (56) References JP-A-49-127916 (JP, A)
Claims (2)
保護基を有してもよい水酸基、Ｘは１以上の保護基を有
してもよい酸性アミノ酸残基を表す。〕 で表される化合物及びその薬学的に許容される塩。1. A compound of the general formula (I): [Wherein, R represents a hydrogen or amino protecting group, Y represents a hydrogen or a hydroxyl group optionally having a protecting group, and X represents an acidic amino acid residue optionally having one or more protecting groups. And a pharmaceutically acceptable salt thereof.
保護基を有してもよい水酸基、Ｘは１以上の保護基を有
してもよい酸性アミノ酸残基を表す。〕 で表される化合物又はその薬学的に許容される塩の少な
くとも一種を有効成分として含有する植物生長調整剤。2. Formula (I): [Wherein, R represents a hydrogen or amino protecting group, Y represents a hydrogen or a hydroxyl group optionally having a protecting group, and X represents an acidic amino acid residue optionally having one or more protecting groups. ] A plant growth regulator containing at least one compound represented by the formula or a pharmaceutically acceptable salt thereof as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63260239A JP2585079B2 (en) | 1987-10-16 | 1988-10-14 | New dipeptide compounds |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26243787 | 1987-10-16 | ||
| JP62-262437 | 1987-10-16 | ||
| JP63260239A JP2585079B2 (en) | 1987-10-16 | 1988-10-14 | New dipeptide compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02254A JPH02254A (en) | 1990-01-05 |
| JP2585079B2 true JP2585079B2 (en) | 1997-02-26 |
Family
ID=26544516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63260239A Expired - Lifetime JP2585079B2 (en) | 1987-10-16 | 1988-10-14 | New dipeptide compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2585079B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1894769B1 (en) | 2005-03-31 | 2012-08-29 | TS Tech Co., Ltd. | Seat height adjustment device for automobile |
| JP4899206B2 (en) * | 2005-03-31 | 2012-03-21 | テイ・エス テック株式会社 | Automotive seat height adjustment device |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5133529B2 (en) * | 1973-04-23 | 1976-09-20 |
-
1988
- 1988-10-14 JP JP63260239A patent/JP2585079B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02254A (en) | 1990-01-05 |
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