JP2005112867A - 非常に大規模な固定化ペプチド合成 - Google Patents
非常に大規模な固定化ペプチド合成 Download PDFInfo
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- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
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- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
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Abstract
【解決手段】 単一の基体表面上の既知の位置で種々の化学的配列を製造する方法であって、(1)(a)基体表面上の選択された領域を照射に暴露することにより保護基を除去し、(b)領域を、照射除去可能な保護基を有する選択されたモノマーに暴露し、選択されたモノマーは、領域の保護基が除去された部分において結合する、ことを含んで成る段階;並びに(2)選択された領域と選択されたモノマーとを用いて上記の段階を反復することを含んで成る方法。
【選択図】 なし
Description
I.用語集
II.一般
III.ポリマー合成
IV.反応器系の1態様の詳細
V.蛍光検出装置の1態様の詳細
VI.受容体の相対結合強度の決定
VII.実施例
A.スライドの調製
B.「A」及び「B」の8種のトライマーの合成
C.アミノ保護基及び蛍光基のダイマーの合成
D.シグナルの可能性の証明
E.単位面積当り分子の数の証明
F.NVOCの除去及び蛍光標識の付加
G.NVOCの除去におけるマスクの使用
H.YGGFLの付加並びにこれに続くHerz抗体及びヤギ抗マウスヘの暴露
I.YGGFLのモノマー並列形成及びそれに続く標識された抗体への暴露
J.YGGFL及びPGGFLのモノマー並列合成
K.YGGFL及びYPGGFLのモノマー並列合成
L.16種類の異るアミノ酸配列の並列の合成及びHerz抗体に対する相対結合親和性の評価
VIII.具体例の例示
IX.結論
I.用語集
次の用語は、これらが本明細書において使用される場合、下記の一般的意味を有する。
リガンド分子及びその受容体の相互作用する表面の形態的(topological)適合性又は一致性に関する。すなわち、受容体とそのリガンドは相補的であると記述することができ、そしてそれ故にその接触表面特性は相互に相補的である。
抗体として知られる受容体のサブクラスとの相互作用領域により描写される抗原分子の部分。
リガンドは特定の受容体により認識される分子である。本発明により研究され得るリガンドの例には、限定的ではないが、細胞膜受容体に対するアゴニスト及びアンタゴニスト、毒素(toxin及びvenom)、ウイルスエピトープ、ホルモン(例えば、鎮静剤、あへん剤、ステロイド等)、ホルモン受容体、ペプチド、酵素、酵素基質、補因子、薬物、レクチン、糖、オリゴヌクレオチド、核酸、オリゴサッカライド、蛋白質、及びモノクローナル抗体が含まれる。
一緒に連結してポリマーを形成することができる小分子のセットの構成質。モノマーのセットは限定的ではないが例えば通常のL−アミノ酸のセット、D−アミノ酸のセット、合成アミノ酸のセット、ヌクレオチドのセット、並びにペントース及びヘキソースのセットが含まれる。本明細書において使用する場合、モノマーはポリマーの合成のための基本セットのいずれかの構成員に関する。例えば、L−アミノ酸のダイマーはポリペプチドの合成のための400のモノマーの基本セットを構成する。モノマーの異る基本セットはポリマーの合成における逐次段階で使用されるであろう。
モノマーがα−アミノ酸でありそしてアミド結合を介して一緒に結合しているポリマーであって、ポリペプチドとも称する。この明細書の文脈において、アミノ酸はL−光学異性体又はD−光学異性体であり得る。ペプチドは2より多くのアミノ酸モノマーの長さを有し、そしてしばしば20より多くのアミノ酸モノマーの長さを有する。アミノ酸のために標準的略号が用いられる(例えば、プロリンについてはP)。これらの略号はStryer,Biochemstry、第3版、1988に含まれており、これをすべての目的のために引用により本明細書に組み入れる。
例えば、電子ビーム放射、γ−放射、X−線放射、紫外線放射、可視光、赤外線放射、マイクロウエーブ放射及びラジオ波を包含する10−14メートル及び104メートルの間の波長を有するエネルギーを含めて、選択的に適用され得るエネルギー。「照射」とは、表面への放射の適用を意味する。
所与のリガイドに対する親和性を有する分子。受容体は天然分子でも人造分子でもよい。さらに、これらはその変化していない状態で又は他の種との凝集体として用いることができる。受容体は共有結合により又は非共有結合により、直接に又は特定の結合物質を介して結合員に付加され得る。本発明により使用され得る受容体の例には、限定的ではないが、抗体、細胞膜受容体、特定の抗原決定基(例えばウイルス、細胞又は他の材料上にあるもの)と反応するモノクローナル抗体及び抗血清、薬物、ポリヌクレオチド、核酸、ペプチド、補因子、レクチン、糖、ポリサッカライド、細胞、細胞膜、及びオルガネラが含まれる。受容体は時として当業界において抗−リガンドとも称される。本明細書において受容体なる用語が使用される場合、意味の相違は意図されない。2つの巨大分子が分子認識を介して結合して複合体を形成する場合、「リガンド受容体対」が形成される。
微生物の生存に必須な特異的輸送蛋白質又は酵素のごとき、受容体に結合するリガンドの決定は新しいクラスの抗生物質において有用である。特に価値あるものは、日和見真菌、原生動物、及び現在使用されている抗生物質に対して耐性を有する細菌に対する抗生物質であろう。
例えば、神経伝達物質の開裂を担当する酵素のごとき酵素の結合部位;異る神経伝達物質を開裂せしめる酵素の作用を変更するある種の受容体に結合するリガンドの決定は、神経伝達の不全の治療において使用され得る薬剤の開発において有用である。
例えば、本発明は、注目の抗原のエピトープと結合する抗体分子上のリガンド結合部位の研究において有用であり、抗原性エピトープを模倣する配列の決定はワクチンの開発を導くことができ、該ワクチンの免疫原は1又は複数のこの様な配列に基き、あるいは前記決定は療法的処置において、例えば自己免疫疾患に対して(例えば「自己」抗体の結合をブロックすることにより)有用な関連診断剤又は化合物の開発を導くことができる。
核酸の配列を合成してDNA又はRNA結合配列を樹立することができる。
1又は複数の反応体の1又は複数の生成物への転換を含む化学反応を促進することができるポリマー、好ましくはポリペプチド。この様なポリペプチドは一般に少なくとも1つの反応体又は反応中間体に対して特異的な結合部位、及び該結合部位の近くにある活性官能基を含み、この官能基は結合した反応体を化学的に変形することができる。触媒的ポリペプチドは例えば米国特許出願No.404, 920に記載されており、これをすべての目的のため引用により本明細書に組み入れる。
例えば、インシュリン及び成長因子のための受容体。高い親和性をもって受容体に結合するリガンドの決定は、例えば、糖尿病の症状の救済のために糖尿病患者がとらなければならない日常的注射に代る経口投与の開発、及び他の場合、死体から又は組換えDNA技法によってのみ得ることができる少ないヒト成長ホルモン代替において有用である。他の例は血管収縮ホルモン受容体であり、受容体に結合するリガンドの決定は血圧を制御する薬剤の開発を導くであろう。
脳におけるあへん受容体に結合するリガンドの決定はモルフィン及び関連薬剤の耽溺性の少ない代替物の開発において有用である。
硬質又は半硬質表面を有する材料。多くの態様例においては基体の少なくとも1つの表面は実質的に平らであるが、幾つかの態様においては、異るポリマーのための合成領域を例えばウエル、隆起した領域、エッチングされた溝等により物理的に分離するのが望ましい。他の具体例に従えば、合成の完了の後に放出される小ビーズを表面に備えることができる。
モノマーユニットに結合しており、そして電磁放射のごときアクチベーターへの暴露に際して空間的に除去される材料。本発明において用途を有する保護基の例にはニトロベーラトリルオキシカルボニル(Nitroveratryloxycarbonyl)、ニトロベンジルオキシカルボニル、ジメチルジメトキシベンジルオキシカルボニル、5−ブロモ−7−ニトロインドリニル、o−ヒドロキシ−α−メチルシンナモイル、及び2−オキシメチレンアンスラキノンが含まれる。アクチベーターの他の例にはイオンビーム、電界、磁界、電子ビーム、X−線等が含まれる。
所定の領域とは、ポリマーの形成のために活性化されたか、活性化されているか、又は活性化されることが意図される表面上の位置決定された領域である。所定の領域は任意の便利な形状、例えば円形、長方形、楕円形、くさび形等を有することができる。本明細書において簡略化のため、「所定の領域」を時として単に「領域」と称する。
基体の1つの所定の領域がそれを他の所定の領域から区別する特性を示す場合、ポリマーは所定の領域内で「実質的に純粋である」と考えられる。典型的には純度は、均一な配列の結果としての生物学的活性又は機能として測定されるであろう。この様な特性は典型的には選択されたリガンド又は受容体との結合により測定されるであう。
本発明は、複数の所定の領域に複数のポリマー配列を有する基体の調製及び使用のための方法及び装置を提供する。本発明はこの明細書において主として、アミノ酸の配列を含む分子の製造に関して記載されるが、しかし他のポリマーの製造にも容易に適用することができる。この様なポリマーには、例えば、核酸の直鎖状及び環状ポリマー、ポリサッカライド、リン脂質、α−、β−又はω−アミノ酸を有するペプチド、上記のいずれかに既知の薬物が共有結合しているヘテロポリマー、ポリウレタン、ポリエステル、ポリカーボネート、ポリウレア、ポリアミド、ポリエチレンイミン、ポリアリ−レンスルフィド、ポリシロキサン、ポリイミド、ポリアセテート、あるいはこの開示の概観の後に明らかになるであろう他のポリマーが含まれる。好ましい態様において、本発明はペプチドの合成に使用される。
S−L−M1−Pl
を含んで成り、他方表面の残りの領域は次の配列:
S−L−PO
を含んで成る、次に、表面の第二領域(これは第一領域を含むことができる)を光に暴露し、そして保護基P2を有する第二モノマーM2(これはM1と同一でもよく、又は異っていてもよい)と接触せしめる。P2はPO及びP1と同一でもよく、又は異っていてもよい。この第二サイクルの後、基体の異る領域は次の配列:
S−L−M1−M2−P2
S−L−M2−P2
S−L−M1−P1 及び/又は
S−L−PO
の1又は複数を含んで成るであろう。基体が所望の長さめ所望のポリマーを含有するまで上記の工程を反復する。光に暴露される基体の場所及び暴露に続き基体に暴露される試薬を制御することにより、各配列の場所が知られるであろう。
S−〔L〕−(Mi)−(Mj)−(Mk)…(Mx)−〔C〕
(式中、中カッコ〔 〕は場合によっては存在する基を示し、そしてMi…Mx
はモノマーの任意の配列を示す)
により示される複数のポリマーを持つ表面を有する基体をもたらす。モノマーの数は広範囲の値にわたることができるが、しかし好ましい態様においてはそれは2〜100の範囲であろう。
図1はこの明細書に開示される本発明の1つの態様を示し、ここでは基体2が断面として示される。本質的に、任意の便利な基体を本発明において使用することができる。基体は生物学的、非生物学的、有機、無機、又はこれらの任意の組合わせであることができ、粒子、ストランド、沈澱、ゲル、シート、チューブ、球状体、容器、毛細管、パッド、スライス、フィルム、プレート、スライド等として存在する。基体は任意の便利な形態、例えばディスク、正方形、円等であることができる。基体は好ましい平らであるが、他の種々の表面構造を取るであろう。例えば、基体はその上で合成が行われる隆起した又はくぼんだ領域を含むことができる。基体及びその表面は好ましくは、本明細書に記載する反応がその上で起る硬質の支持体を形成する。基体及びその表面はまた、適切な吸光特性を与えるように選択される。例えば、基体は、重合したラングミューア・ブロジェットフィルム(Langmuir Bludgett)フィルム、官能化されたガラス、Si,Ge,GaAs,GaP,SiO2、SiN4、改質シリコン、又は広範囲の種類のゲル又はポリマー、例えば(ポリ)テトラフルオロエチレン、(ポリ)ビニリデンジフルオリド、ポリスチレン、ポリマーボネート、又はこれらの組合せであることができる。他の基体材料はこの開示を概観した後に当業者にとって明らかであろう。好ましい態様において、基体は10Å未満の表面レリーフ特性を有する単結晶シリコン又は平らなガラスである。
IV.反応器系の1つの態様の詳細
図8は、本発明の1つの観点に従って調製された基体上にポリマーを合成するための反応器系100の好ましい態様を示す。この反応器系はその表面上に空洞104を有する体部102を含む。好ましい態様においては空洞は約50〜1000μmの深さを有し、約500μmの深さが好ましい。
Basicの単純なコンピュータープログラムを提供する。プログラムのアウトプットは、セルの数、各マスク上の「strips」(光領域)の数、及びマスクの各暴露のために必要な移動の量である。
図10は基体上の蛍光標識された受容体を検出するための蛍光検出装置を示す。基体112はx/y移動テーブル202の上に置かれる。好ましい態様においては、x/y移動テーブルはニューポート社(New port Corporation)により製造されるモデルNo.PM500−A1である。x/y移動テーブルは、例えば適切にプログラムされたIBM PC/AT又はAT適合コンピューターであってもよい適切にプログラムされたデジタルコンピューター204に接続されそしてそれにより制御される。
VI.受容体の早退結合強度の決定
本発明のシグナル対ノイズ比は十分に高く、リガンドに対する受容体の存在又は不存在が検出され得るのみならず、種々の配列に対する受容体の相対的結合親和性を決定することができる。
VII.例
次の例は本発明の有効性を説明するために提供される。すべての操作は、特にことわらない限りおよそ周囲温度及び圧力において行われた。
A.スライドの調製
反応性基の結合の前に、好ましい態様においては顕微鏡スライド又はカバースリットのごときガラス製基体である基体を清浄にするのが好ましい。1つの態様に従えば、例えば120mlの水及び120gの水酸化ナトリウムを含む95%エタノール11から成るアルカリ浴にスライドを12時間浸漬する。次にスライドを流水で洗浄しそして空気乾燥し、そして95%工タノールの溶液で一度すすぐ。
B.「A」及び「B」の8種のトリマーの合成
図11は、2−モノマーセット:Gly及びPhe(それぞれ、「A」及び「B」により示す)の8種のトリマーの可能な合成を示す。6−ニトロべラトリルオキシカルボキサミド(NVOC−NH)残基で終るシラン基を担持するガラススライドを基体として調製する。アミノ基においてNVOCにより保護されたg1y及びpheの活性エステル(ペンダフルオロフェニル、OBt)等を試薬として調製する。この例には関係ないが、モノマーセットのために側鎖保護基が必要な場合、これらは主鎖を保護するために使用される光の波長において光反応性であってはならない。
1.次の残基が付加されるべき部位でのアミノ基の露出のための適当なマスクを通しての照射、及び脱保護の副生成物を除去するための適切な洗浄。
n×l (1)
により定義され、ここで
n=モノマーのべースセット中のモノマーの数、及び
l=ポリマー鎖中のモノマーユニットの数、
である。
nt (2)
である。
nt+nt−1+…+n1 (3)
であろう。
合成領域のサイズ=(A/S)
であり、ここで
Aは合成のために利用可能な全面積であり、そして
Sはこの全面積において望まれる配列の数である。
C.アミノプロピル基及び蛍光基のダイマーの合成
アミノプロピル基及び蛍光基のダイマーの合成において、基体として官能化されたドラポア(durapore)膜を用いた。ドラポア(durapore)膜はアミノプロピル基を有するポリビニリデンジフルオリドである。アミノプロピル基を、カルボニルクロリドとアミノ酸との反応によりDDZ基によって保護した、この反応は当業者によく知られた反応である。
D.シグナル可能性の証明
シグナル検出の可能性が、フロー・サイトメトリー・スタンダーダ(Flow
Cytometry Standard)により製造されたモデルNo.824の低レベル標準蛍光ビーズキットを用いて証明された。このキットは、既知の数の蛍光分子が含浸された直径5.8μmのビーズを含む。
E.単位面積当り分子の数の決定
前記の方法に従って調製されたアミノプロピル化ガラス顕微鏡スライドを用いて該スライドの標識化密度を確立した。スライドの遊離アミノ末端を、該アミノ基と共有結合を形成するFITC(フルオレッセインイソチオシアネート)と反応せしめた。次に、スライドをスキャンニングして、フルオレッセント分子当り光子の予想値を用いて、単位面積当り表面上の分子の数の計算を可能にする領域中に発生するフルオレッセント光子の数をカウントする。
F.NVOCの除去及び蛍光標識の付加
NVOC−GABAを前記のようにして付加した。1個のスライドの全表面を光に暴露してγ−アミノ酪酸の末端の遊離アミノ基を露出した。次に、このスライド及び暴露されていない同じものをフルオレッセインイソチオシアネート(FITC)に暴露した。
G.NVOCの除去におけるマスクの使用
次の実験を0.1%アミノプロピル化スライドを用いて行った。Hg−Xeアーク灯からの光を、レーザー切除したガラス上クロムマスクを通して、基体を直接接触させることにより基体上に像形成した。
H.YGGFLの付加、並びにこれに続くHerz抗体及びヤギ抗マウスへの暴露
特定のポリペプチド配列に対する受容体が表面結合ペプチドに結合しそして検出されることを確立するために、Leuエンケファリンを表面に結合させそして抗体により認識させた。スライドを0.1%アミノプロピル−トリエトキシシランにより誘導体化し、そしてNVOCにより保護した。裏側接触印刷(back
side contact printing)を用いて流れセル中のスライドを暴露するため500μmチェッカーボードを用いた。
I.YGGFLのモノマー並列形成及びそれに続く標識抗体への暴露
交互の正方形におけるYGGFL及びGGFLのモノマー並列合成をスライド上チェッカーボードパターン中で行い、そして得られるスライドをHerz抗体に暴露した。この実験を図16及び図17に示す。
J.YGGFL及びPGGFLのモノマー並列合成
図16及び17に示したものに類似する50μmチェッカーボードマスクを用いての合成を行った。しかしながら、追加の連結段階を通して基体上のGGFL部位にPを加えた。保護されたGGFLをマスクを通して光に暴露し、そして次に、前記のようにしてPに暴露することによりPを付加した。従って、基体上の領域の半分はYGGFLを含有し、そして残りの半分はPGGFLを含有した。
K.YGGFL及びYPGGFLのモノマー並列合成
本発明の機能可能性をさらに示すため、前記のような技法を用いて基体上に交互のYGGFL及びYPGGFLの50μmチェッカーボードパターンを合成した。得られる蛍光プロットが示すところによれば、抗体はYGGFL配列を明瞭に認識することができそしてYPGGFL領域には有意に結合しなかった。
L.一連の16種類の異なるアミノ酸配列の合成及びHerz抗体への相対結合親和性の評価
前記の技法に類似する技法を用いて、一連の16種類の異るアミノ酸配列(4連反復)を2枚のガラス基体のそれぞれの上で合成した。スライドの全表面にわたって配列NVOC−GFLを付加することにより配列を合成した。次に、一連のマスクを用いて2層のアミノ酸を基体に選択的に適用した。各領域は0.25cm×0.0625cmの寸法を有していた。第一のスライドはL−アミノ酸のみを含むアミノ酸配列を含んでおり、そして第二のスライドは選択されたD−アミノ酸のみを含んだ。図18のA及び図18のBはそれぞれ第一スライド及び第二スライド上の種々の領域のマップを示す。図18のA及び図18のBに示されるパターンは各スライド上に4連反復させた。次に、スライドをHerz抗体及びフルオレッセイン−標識ヤギ抗−マウスに暴露した。
本発明の他の態様に従えば、この方法は、表面への囲まれた(caged)結合員の結合を提供し、この結合員はその囲まれた形態において、他の潜在的に結合する種、例えば受容体及び特異的結合基質に対する比較的低い親和性を有する。この様な技法は、1989年9月8日出願の係続中の出願No.404,920にさらに十分に記載されており、これをすべての目的のため引用により本明細書に組み入れる。
IX.結論
本発明は、基体上でポリマーを合成するための非常に改良された方法及び装置に関する。前記の記載は例示的なものであって制限的なものではないことが意図される。前記の記載を概観した後、当業者には多くの態様が自明であろう。例として、本発明は主として光除去可能な保護基の使用に言及して記載しているが、光以外の他の放射源を使用し得ることが当業者に容易に認識されるであろう。例えば、幾つかの態様において、電子ビーム照射、X−線照射(電子ビームリソグラフとの組合せにおける)、又はX−線リソグラフィー技法に対して選択的である保護基を用いるのが望ましいであろう。あるいは、電流への暴露により基を除去することができよう。従って本発明の範囲は、前記の記載によって決定されるべきではなく、添付された請求の範囲及び該請求の範囲に均等な全範囲に関して決定されるべきである。
Claims (1)
- 単一の基体表面上の既知の位置で種々の化学的配列を製造する方法であって、 (1)(a)前記基体表面上の選択された領域を照射に暴露することにより保護基を除去し、 (b)前記領域を、照射除去可能な保護基を有する選択されたモノマーに暴露し、該選択されたモノマーは、該領域の保護基が除去された部分において結合する、ことを含んで成る段階;並びに (2)選択された領域と選択されたモノマーとを用いて上記の段階を反復すること、 ここで各反復段階における選択された領域は、先行する段階における選択された領域と同一であるか、部分的に重複するか、又は異る領域であり、そして各反復段階における選択されたモノマーは、先行する段階のそれと同一であるか又は異っており、そして、各反復段階における領域及びモノマーは、該モノマーが該領域の基体表面上の保護基または先行する段階のモノマーの保護基が除去された部分において結合するように選択され、 該反復段階により、それぞれ2つ以上のモノマーを含んで成る種々の配列が前記基体上に合成される、を含んで成る方法。
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1990
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