JPS58159451A - Amide derivative and gas chromatographic analytical method for enantiomeric mixture by using said amide derivative as stationary phase - Google Patents
Amide derivative and gas chromatographic analytical method for enantiomeric mixture by using said amide derivative as stationary phaseInfo
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- JPS58159451A JPS58159451A JP57043603A JP4360382A JPS58159451A JP S58159451 A JPS58159451 A JP S58159451A JP 57043603 A JP57043603 A JP 57043603A JP 4360382 A JP4360382 A JP 4360382A JP S58159451 A JPS58159451 A JP S58159451A
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- Prior art keywords
- amide derivative
- naphthyl
- acid
- group
- mandelic acid
- Prior art date
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は新規な不斉アミド誘導体およびそれをガスクロ
マトグラフィーの固定相に用いて、不斉炭素に結合した
一冊一基、−０ＯＮＨ−基、−ＯＨ基、−ＣＮ基あるい
は−ｃｏｏ−基を有する化合物の鏡像体混合物を分離し
、分析する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention provides a novel asymmetric amide derivative and its use in the stationary phase of gas chromatography. The present invention relates to a method for separating and analyzing a mixture of enantiomers of a compound having a CN group or a -coo- group.
不斉炭素を有する化合物の鏡像体混合物をガスクロマト
グラフィーにより直接分離し、分析するだめの光学活性
固定相としてカルボン酸アミドが有効なことはよく知ら
れており、たとえばＮ−ラウロイル−（Ｓ）−／−（α
−ナフチル）エチルアミン〔Ｓ、Ｗｅｉｎｓｔｅｉｎ等
、 Ｊ、ＣｈｒＯｍａｔｏｇｒ 、。It is well known that carboxylic acid amides are effective as optically active stationary phases for directly separating and analyzing enantiomeric mixtures of compounds with asymmetric carbon atoms by gas chromatography; for example, N-lauroyl-(S) −/−(α
-naphthyl)ethylamine [S, Weinstein et al., J. ChrOmatogr.
ろ弦、 ９７ Ｃ／９７乙）〕や〇−置換マンデル酸の
／−フェニルエチルアミドあるいはｔｅｒｔ−ブチルア
ミド〔Ｗ、Ａ、Ｋｉ１５ｎｉｇ等、 Ｊ、０１ｒｏｍａ
ｔｏｇｒ、、 ２ｔ）０ 、７ｇり（／９にθ）〕など
が報告されている。また、本発明者等は第−葉酸等の／
−（α−ナフチル）エチルアミド〔天井ら、 Ｊ、Ｃｈ
ｒｏｍａｔｏｇｒ 、 、 ２／３ 、 ／３７（／？
ｇ／）〕やマンデル酸等の／−（α−ナフチル）エチル
アミド〔天井ら２日本分析化学会第３０年会講演要旨集
、ｐ’３’ｌＳ Ｃ／９ｇｏ）京都〕を固定相とする鏡
像体混合物の分離、分析法を見出した０しかしながら、
上記各固定相は不斉炭素に結合した一ＮＨ−基、−００
ＮＨ−基、−ＯＨ基あるいは一〇Ｎ基を有する化合物の
鏡像体混合物の分離には優れた威力を発揮するものの不
斉炭素に結合したーＣｏ〇−基を有する化合物の鏡像体
混合物の分離はわずかに〇−置換マンデル酸の／−フェ
ニルエチルアミドあるいはｔｅｒｔ−ブチルアミドによ
る０〜トリフルオロアセチル−マンデル酸のイソプロピ
ルエステルの分離や第−葉酸の／−（α−ナフチル）エ
チルアミドによるシスー菊酸のエチルエステル等の分離
等が報告されているにすぎない。しかも、この分離にお
ける分離係数は槓めて小さく、これらの固定相の最高使
用温度の低いこともあって、実用的な固定相とは言い難
い。97C/97O)] and/-phenylethylamide or tert-butyramide of 〇-substituted mandelic acid [W, A, Ki15nig, etc., J, 01roma
togr, 2t)0, 7gr(θ to /9)], etc. have been reported. In addition, the present inventors have also discovered that folic acid, etc.
-(α-naphthyl)ethylamide [Tenyo et al., J, Ch
romatogr, , 2/3, /37(/?
g/)] or mandelic acid, etc., using /-(α-naphthyl)ethylamide [Tenyo et al. 2, Abstracts of the 30th Annual Meeting of the Japanese Society of Analytical Chemistry, p'3'lS C/9go) Kyoto] as the stationary phase. discovered a method for separating and analyzing body mixtures.
Each of the above stationary phases has one NH- group bonded to an asymmetric carbon, -00
Although it is effective in separating enantiomeric mixtures of compounds having NH-, -OH, or 10N groups, it is difficult to separate enantiomeric mixtures of compounds having -Co〇- groups bonded to an asymmetric carbon. The separation of isopropyl ester of 0-trifluoroacetyl mandelic acid using /-phenylethylamide or tert-butylamide of 〇-substituted mandelic acid, and the separation of cis-chrysanthemum acid using /-(α-naphthyl)ethylamide of tertiary folic acid Only separation of ethyl ester, etc. has been reported. Moreover, the separation coefficient in this separation is extremely small, and the maximum operating temperature of these stationary phases is low, so it is difficult to call them practical stationary phases.
木発明者らはかかる状況のもとて不斉炭素に直結した−
０００−基を有する化合物の鏡（＃体温合物を分離し得
る固定相の開発を目標に鋭意検討を続けた結果、光学活
性なノー（α−ナフチル）エチルアミン、光学活性かマ
ンデル酸および光学活性な第−葉酸とから成る不斉なア
ミド誘導体が、不斉炭素に直結した一ＣＯ〇−基を有す
る化合物の鏡像体混合物の分離に優れた効果を示すのみ
ならず、不斉炭素に直結した一皿一基、−ｃＯＮＢ−基
、−（）Ｈ基あるいけ−ＣＮ基を有する化合物の鏡像体
混合物をも分離し得ることを見出し５本発明に至ったも
のである。Under such circumstances, the wood inventors directly connected to the asymmetric carbon.
As a result of intensive research aimed at developing a stationary phase capable of separating mirror (# temperature) compounds of compounds having 000-groups, we discovered optically active no-(α-naphthyl)ethylamine, optically active or mandelic acid, and optically active mandelic acid. An asymmetric amide derivative consisting of primary folic acid not only shows excellent effects in separating enantiomeric mixtures of compounds having one CO〇- group directly connected to an asymmetric carbon, but also shows excellent effects in separating enantiomeric mixtures of compounds having one CO〇- group directly connected to an asymmetric carbon. The present invention was based on the discovery that enantiomeric mixtures of compounds having a -cONB- group, a -()H group, or a -CN group can be separated one by one.
（３）
即ち１本発明は一般゛式〔Ｉ〕
〔式中、※け不斉炭素を表わし、酸成分の第−葉酸およ
びマンデル酸およびアミン成分である／−（α−ナフチ
ル）エチルアミンはいずれも光学活性体である。〕
で示される不斉がアミド誘導体およびそれをガスクロマ
トグラフィーの固定相に用いて、不斉炭素に結合し六−
１基、−００ＮＨ−基、 −ＯＨ基、 −ＯＨ基または
−０００−基を有する化合物の鏡像体混合物を分離し、
分析する方法を提供するものである。(3) That is, 1 the present invention has the general formula [I] [wherein * represents an asymmetric carbon, the acid components are folic acid and mandelic acid, and the amine component is /-(α-naphthyl)ethylamine. is also an optically active substance. ] An amide derivative with the chiral structure shown in
separating an enantiomeric mixture of a compound having one group, -00NH- group, -OH group, -OH group or -000- group,
It provides a method for analysis.
一般式［１）で示される不斉なアミド誘導体において、
マンデル酸部分は（ト）または←）のマンデル酸、第−
葉酸部分は（イ）および／または←）のシスおよび／″
！たはトランスの第−葉酸、アミン部分Ｖｉ（ト）マタ
は←）の／−（α−ナフチル）エチルアミンが好適であ
る０
前記一般式［Ｉ）で示される不斉なアミド誘導（り ）
体は（４−１オたは←）のマンデル酸と（ト）またに、
←）の／−（α−ナフチル）エチルアミンから既知のア
ミド化反応により得られたマンデル酸の／−（α−ナフ
チル）エチルアミドを（ト）および／または←）のシス
および／ｌた１士トランス−葉酸とのエステル化反応に
より容易に合成する。ことができる。In the asymmetric amide derivative represented by general formula [1],
The mandelic acid moiety is (g) or ←) mandelic acid,
The folic acid part is (a) and/or ←) cis and /″
! or trans-folic acid, and the amine moiety Vi(t)mata is preferably /-(α-naphthyl)ethylamine of ←). is (4-1o or ←) mandelic acid and (g) also,
/-(α-naphthyl)ethylamide of mandelic acid obtained by a known amidation reaction from /-(α-naphthyl)ethylamine of ←) and/or cis and /l of mandelic acid -Easily synthesized by esterification reaction with folic acid. be able to.
本発明になる不斉なアミド誘導体の代表例を以下に示す
。Representative examples of the asymmetric amide derivatives of the present invention are shown below.
化合物（ハ
０−…−トランスーー、、２−ジメチル−５−（、！−
メチルプロペニル）シクロプロパン−／−カルボニル−
（ト）−マンデル酸 ０→−／−（α−ナフチル）エチ
ルアミド
元素分析値
ＣＸ＠ Ｈ（＠Ｎ（イ）
実測値 ７ｇ、乙 ７．１１ ３．θ化合物
（２）
０−（ト）−トランス−２，コージメチル−５−（２−
メチルプロペニル）シクロプロパン−／−カルボニル−
ｆ−）−）−マンデル酸 （−） −／ −（α−す７
チル）エチルアミド
融点：にθ〜１０オ°Ｃ
〔“〕６°：＋乙００（Ｃ＝０．３乙係、クロロホルム
）元素分析値
Ｃ（係） Ｈ（係） Ｎ（憾）
実 測 値 ７Ｊ’、９ ７．４ ３
刀計 算 値 η、／ ７．３ ３
．／（Ｃ３０Ｈ３３ＮＯ３として）
本発明によって得られた不斉なアミド誘導体をガスクロ
マトグラフィーの固定相に使用し、不斉炭素に結合した
ー■−基、−（１りＮＨ−基、−〇Ｈ基、−ＯＮ基ある
いは一〇〇〇−基を有する化合物の鏡像体混合物を分離
し、分析する場合、従来一般に用因られている種々の方
法がその捷寸適用できるが、この種の化合物の鏡像体混
合物の分離件数は小さいことが多く、実用的か分離を達
成するためには理論段数を向上させることが容易で、分
雅卵の優れたキャピラリーカラムが好適である。Compound (ha0-...-trans-,,2-dimethyl-5-(,!-
methylpropenyl) cyclopropane-/-carbonyl-
(t)-mandelic acid 0→-/-(α-naphthyl)ethylamide elemental analysis value CX@H(@N(i) Actual value 7g, Otsu 7.11 3.θ compound (2) 0-(t)- trans-2, cordimethyl-5-(2-
methylpropenyl) cyclopropane-/-carbonyl-
f-)-)-mandelic acid (-) -/-(α-su7
(C) Ethylamide melting point: θ ~ 10 °C ["] 6 °: +00 (C = 0.3, Chloroform) Elemental analysis value 7J', 9 7.4 3
Sword calculation value η, / 7.3 3
．． /(as C30H33NO3) The asymmetric amide derivative obtained by the present invention was used as a stationary phase for gas chromatography, and the -■- group, -(1NH- group, -〇H group) bonded to the asymmetric carbon When separating and analyzing a mixture of enantiomers of a compound having , -ON group or 1000- group, various methods commonly used in the past can be applied to the separation. The number of separations of body mixtures is often small, and in order to achieve practical separation, it is easy to increase the number of theoretical plates, and Bunya Egg's excellent capillary column is suitable.
ｌｕ下、実施例によって本発明を具体的に説明する力“
、本発明けこれらに限定される本のではな込ことは言う
までもかい。The power to concretely explain the present invention by way of examples is given below.
It goes without saying that the present invention is not limited to these.
実婢例／
（＋）−マンデル酸−０ｘｇにｆ−）−） −／ −（
α−ナフチル）エチルアミン、２．Ｊ？ ９分よび脱水
テトラヒドロ７ラン３θｄを加えて溶かし、氷冷しなか
らＮ、Ｎ’−ジシクロへキシルカルボジイミド３．３ｇ
およびＮ−ヒドロキシメンシトリアゾール２．３ｆｌを
加え、水冷下コ時間、さらに室温でΩ時間攪拌した。−
夜放置後、減圧下で溶媒を留去し、残留物を酸およびア
ルカリ水で洗浄し、汁）−マンデル酸 ［４−） −／
−（α−す７チル）エチルアミドの粗製物グ、１ｇを
得た。この粗製物をシリカゲルク日マド（７）
グラフィー（溶離液：クロロホルム）によｈ精製し、白
色、固体の精製（＋）−マンデル酸汗）−／−（α−ナ
フチル）１手ルアミド／、１ｇを得た。Practical example / (+)-mandelic acid-0xg f-)-) -/ -(
α-naphthyl)ethylamine, 2. J? After 9 minutes, add dehydrated tetrahydro 7ran 3θd to dissolve, cool on ice, and add 3.3 g of N,N'-dicyclohexylcarbodiimide.
and 2.3 fl of N-hydroxymencitriazole were added thereto, and the mixture was stirred for several hours under water cooling and further stirred at room temperature for several hours. −
After standing overnight, the solvent was distilled off under reduced pressure, the residue was washed with acid and alkaline water, and the solution was extracted with mandelic acid [4-) -/
1 g of crude -(α-7thyl)ethylamide was obtained. This crude product was purified by silica gel chromatography (eluent: chloroform) to give a white solid (+)-mandelic acid sweat)-/-(α-naphthyl) 1-handed amide/, 1g was obtained.
次（八で、この精１！Ｂ（−４−）−マンデルｅ （＋
１−／−（α−ナフチル）エチルアミドＯ，１，／９に
（ト）−トランス−葉酸りロリドｏ、ｔｇ、ピリジンｏ
、、ｚｙｇおよび脱水ジオキサン／θｒｕｔを加えて溶
かし、沸とう水浴中で２時間加熱したのち溶媒を減圧下
で留去し、残留物を酸およびアルカリ水で洗浄し、０−
（−１−１−トランスークリサンセモイル−（＋）１ン
デル酸 ｆ＋）−／−（α−ナフチル）エチルアミドの
粗製物的／、７ｇを得た。九の粗製物をシリカゲルカラ
ムクロマトグラフィー（溶離液：クロロホルム）により
精製し、白色、固体の精！ｎｏ −ｔ−＋−）−）ラン
スークリサンセモイルー←ト）−マンデル酸（＋ｌ −
／ −（α−ナフチル）エチルアミド〔化合物（１）〕
θ、オｇを得た。このものの構造は元素分析、ＮＭＲ、
ＭＳにより確認された。Next (8, this spirit 1! B (-4-) - Mandel e (+
1-/-(α-naphthyl)ethylamide O,1,/9, (t)-trans-folic acid polyloride o, tg, pyridine o
,,zyg and dehydrated dioxane/θrut were added and dissolved, heated in a boiling water bath for 2 hours, the solvent was distilled off under reduced pressure, the residue was washed with acid and alkaline water, and 0-
7 g of a crude product of (-1-1-trans-chrysansemoyl-(+)1-nderic acid f+)-/-(α-naphthyl)ethylamide was obtained. The crude product of No. 9 was purified by silica gel column chromatography (eluent: chloroform), and a white, solid product was obtained. no -t-+-)-)lansu chrysansemoyl←t)-mandelic acid (+l-
/ -(α-naphthyl)ethylamide [Compound (1)]
θ and og were obtained. The structure of this substance was determined by elemental analysis, NMR,
Confirmed by MS.
（Ｌ！″ ）
次に、と＝で得られた情勢Ｑ−（４−）−トランス−ク
リ廿ンセモイルー（＋）−マンデル酸 汗）−／−（α
−ナフチル）エチルアミドを内径ｏ、、：ｚｓ’ ｗ
、長さくｉ−ｏｍのガラスキャピラリーの内壁に塗布し
、つぎの条件で出−シス、トランスー５−Ｃ２，，２−
ジクロロビニル）−λ。(L!″) Next, the situation obtained with and =
-naphthyl)ethylamide with inner diameter o, :zs' w
, was applied to the inner wall of a glass capillary with a length of i-om, and under the following conditions, cis and trans-5-C2,,2-
dichlorovinyl)-λ.
−一ジメチルンクロプロバンー／−カルボン酸エチルエ
ステルを分析し５図−／のガスクロマトグラムを得た。The gas chromatogram shown in Figure 5 was obtained by analyzing -1-dimethylchloroproban/-carboxylic acid ethyl ester.
ｒ’）Ｊ −／中、ピーク番号（１）は溶媒のクロロホ
ルム、（、，２）ｉま（＋）または（−１−シス−５−
（，２゜ノージクロロビニル）−２，２−ジメチルシク
ロプロパンカルボン酸エチル、（３）は（＠捷−／ｒけ
（＋）−シス−５−（ｊ、、２−ジクロロビニル）−，
２’、 ２−ジメチルシフ１プロパンカルボン酸エチル
、（グ）１寸（＋）号たｔｉｔ （刊−トランス−５−
Ｃ，２，２−ジクロロビニル）−、！、 、２−ジメチ
ルシクロプロパンカルボン酸エチル、そして（−や）は
（＠寸ｆ！、ば（＋） −トランス−５−（２，，２−
ジクロロビニル）−２２，２−ジメチルシクロプロパン
カルボン酸エチルの各ピークである。（２）のピークお
よび（り）のピークが溶出する捷でに要する時間はそれ
ぞれ約ｔｔ ３分および約タデ分であり、分離係数はシ
ス体で／、ＯＭｌ 、トランス体で／、０）！ｌ 、（
，２）と（３）および（＜ｌ）と（オ）のピークの面積
化けそれぞれオ０ ： 、ｆ Ｏおよび！θニオ０であ
った。r')J-/, peak number (1) is the solvent chloroform, (,,2) ima(+) or (-1-cis-5-
(,2゜Nodichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid ethyl, (3) is (@捷-/rKE(+)-cis-5-(j,,2-dichlorovinyl)-,
2', 2-Dimethyl Schiff ethyl propanecarboxylate, (g) 1 sun (+) title (published-trans-5-
C,2,2-dichlorovinyl)-,! , , ethyl 2-dimethylcyclopropanecarboxylate, and (-ya) is (@size f!, ba (+) -trans-5-(2,,2-
These are the peaks of ethyl dichlorovinyl)-22,2-dimethylcyclopropanecarboxylate. The time required for the elution of the peaks (2) and (ri) is approximately 3 minutes and approximately 3 minutes, respectively, and the separation coefficients are 0 for the cis isomer, OMl for the trans isomer, and 0 for the trans isomer! l, (
, 2) and (3) and (<l) and (o) peaks are respectively O0 : , f O and ! θ was 0.
実施で５１２〜グ
固定相として実施例／で得られたｉ′Ｗ製０−（＋）−
トランスークリサンセモイル−（ト）−マンデル酸ｆ＋
）−／−（α−ナフチル）エチルアミド〔化合物（１）
〕を用い、同様にして以下の化合物の鐘イ象体混合絵を
分離し、分離係数を求めた。0-(+)- manufactured by i'W obtained in Example/ as a stationary phase in 512~
trans-chrysansemoyl-(t)-mandelic acid f+
)-/-(α-naphthyl)ethylamide [Compound (1)
] was used to similarly separate the bell-eye mixture picture of the following compounds, and the separation coefficient was determined.
結果を下肥に表記する。Write the results on the bottom manure.
（／／）
μ Ｍ 而 ａ）修 軸１ プシ 香φ 日日実
施例Ｓ〜７
固定相として０− （」→−トランスークリサンｔモイ
ルー（１）−マンデル酸 （→−／−（α−ナフチル）
エチルアミド〔化合物（−２） 〕ｗ用い、実施例／と
同様にして以下の化合物の鏡像体混合物全分離し、分離
係数を求めた。結果全下記に表記する。(//) μ M and a) Modification axis 1 Psi incense φ Day-to-day Example S~7 As the stationary phase 0- (''→-transucrysantmoyl(1)-mandelic acid (→-/-(α- naphthyl)
Using ethylamide [compound (-2)] w, the enantiomeric mixture of the following compound was completely separated in the same manner as in Example 1, and the separation coefficient was determined. All results are listed below.
（／、２）
図／に実施例／Ｖｃおいて（１）−シス、トランス−Ｊ
−（，２，，２−ジクロロビニル）−２２，２−ジメチ
ルシクロプロパンカルボン酸エチルエステルを分析した
時のガスクロマトグラムであり、縦軸は強度全横軸は保
持時間を表わす。(/, 2) Figure/in Example/Vc (1)-cis, trans-J
This is a gas chromatogram when analyzing -(,2,,2-dichlorovinyl)-22,2-dimethylcyclopropanecarboxylic acid ethyl ester, where the vertical axis represents intensity and the horizontal axis represents retention time.
（／、？完）(/, ? complete)
Claims (1)
びマンデル酸およびアミン成分である／−（α−ナフチ
ル）エチルアミンはいずれも光学活性体である。〕 で示される不斉なアミド誘導体。 （Ｐ２）一般式（１〕 〔式中、※は不斉炭素を表わし、酸成分の第−葉酸およ
びマンデル酸およびアミン成分である／−（α−ナフチ
ル）エチルアミンはいずれも光学活性体である。〕 で示される不斉なアミド誘導体を固定相に用いて、不斉
炭素に結合した一ＮＨ−基、−０ＯＮＨ−基、−０Ｈ基
、−ＣＮ基捷たは−Ｃ０〇−基を有する化合物の鏡像体
混合物を分離し、分析することを特徴とするガスクロマ
トグラフィー分析法０(1) General formula [N [In the formula, * represents an asymmetric carbon, and the acid components tertiary folic acid and mandelic acid and the amine component /-(α-naphthyl)ethylamine are all optically active substances. ] An asymmetric amide derivative represented by (P2) General formula (1) [In the formula, * represents an asymmetric carbon, the acid components - folic acid and mandelic acid, and the amine component /-(α-naphthyl)ethylamine are all optically active substances. ] An asymmetric amide derivative represented by is used as a stationary phase, and has one NH- group, -0ONH- group, -0H group, -CN group, or -C00- group bonded to an asymmetric carbon. Gas chromatography analysis method 0 characterized by separating and analyzing an enantiomeric mixture of a compound
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57043603A JPS58159451A (en) | 1982-03-17 | 1982-03-17 | Amide derivative and gas chromatographic analytical method for enantiomeric mixture by using said amide derivative as stationary phase |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57043603A JPS58159451A (en) | 1982-03-17 | 1982-03-17 | Amide derivative and gas chromatographic analytical method for enantiomeric mixture by using said amide derivative as stationary phase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58159451A true JPS58159451A (en) | 1983-09-21 |
| JPH0333703B2 JPH0333703B2 (en) | 1991-05-20 |
Family
ID=12668393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57043603A Granted JPS58159451A (en) | 1982-03-17 | 1982-03-17 | Amide derivative and gas chromatographic analytical method for enantiomeric mixture by using said amide derivative as stationary phase |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58159451A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103439457A (en) * | 2013-08-28 | 2013-12-11 | 南通天泽化工有限公司 | Measurement method for content of 40% DV chrysanthemic acid |
-
1982
- 1982-03-17 JP JP57043603A patent/JPS58159451A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103439457A (en) * | 2013-08-28 | 2013-12-11 | 南通天泽化工有限公司 | Measurement method for content of 40% DV chrysanthemic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0333703B2 (en) | 1991-05-20 |
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