アリールアジドはナイトレンのよく知られた前駆体であり、受容体を研究するための幅広い用途を持つ光アフィニティラベリング剤としてFleetらによって報告されました。
光分解されるとN2が遊離され、非常に不安定な一重項フェニルナイトレンが *in
situ*で形成されます。多様な反応を介して隣接する分子と反応しますが、同時に環拡大反応や同一分子間の結合反応等も生じます。これに対しペルフルオロフェニルアジドは、高収率で隣接基との挿入反応および付加反応を行う非常に安定なナイトレン中間体を形成します。
このタイプの化合物は、エストロゲン受容体研究や炭素系ポリマー、有機系ポリマーの表面コーティングのために光架橋剤(λmax=258nm)として使用されています。これらの化合物は、従来のクリックケミストリー用試薬として、低分子化合物や生体分子の結合のための光活性化リンカー、さらには表面修飾のための反応基導入およびナノマテリアル合成のために使用することが可能であり、応用分野はかなり幅広いものとなります。
参考文献
▷ Affinity of Antibodies with Aryl Nitrenes as Reactive Group; G.W.J. Fleet, R.R. Porter, J.R. Knowles; Nature 1969; 224: 511-512.
▷ Perfluorophenyl Azides: New Applications in Surface Functionalization and Nanomaterial Synthesis; Li-Hong L iu, Mingdi Yan; Accounts of Chemical Research 2011; 43(11): 1434-1443. DOI 10.1021/ar100066t.
製品一覧
表1. 光架橋リンカー製品一覧
| コード |
製品名 |
分子式 |
CAS |
分子量 |
内容量 |
名称 |
| HAA2130.0001 |
N3-L-Dap(Boc)-OH |
C8H14N4O4 |
- |
230.22 |
1g |
(S)-2-Azido-3-((t-butyloxycarbonyl)amino)propanoic acid |
| HAA2130.0005 |
N3-L-Dap(Boc)-OH |
C8H14N4O4 |
- |
230.22 |
5g |
(S)-2-Azido-3-((t-butyloxycarbonyl)amino)propanoic acid |
| HAA2130.0025 |
N3-L-Dap(Boc)-OH |
C8H14N4O4 |
- |
230.22 |
25g |
(S)-2-Azido-3-((t-butyloxycarbonyl)amino)propanoic acid |
| HAA2135.0001 |
N3-D-Dap(Boc)-OH |
C8H14N4O4 |
- |
230.22 |
1g |
(R)-2-Azido-3-((t-butyloxycarbonyl)amino)propanoic acid |
| HAA2135.0005 |
N3-D-Dap(Boc)-OH |
C8H14N4O4 |
- |
230.22 |
5g |
(R)-2-Azido-3-((t-butyloxycarbonyl)amino)propanoic acid |
| HAA2135.0025 |
N3-D-Dap(Boc)-OH |
C8H14N4O4 |
- |
230.22 |
25g |
(R)-2-Azido-3-((t-butyloxycarbonyl)amino)propanoic acid |
| HAA2140.0001 |
N3-L-Dap(Fmoc)-OH |
C18H16N4O4 |
880637-82-1 |
352.34 |
1g |
(S)-2-Azido-3-[(9-fluorenylmethyloxycarbonyl)amino]propanoic acid |
| HAA2140.0005 |
N3-L-Dap(Fmoc)-OH |
C18H16N4O4 |
880637-82-1 |
352.34 |
5g |
(S)-2-Azido-3-[(9-fluorenylmethyloxycarbonyl)amino]propanoic acid |
| HAA2140.0025 |
N3-L-Dap(Fmoc)-OH |
C18H16N4O4 |
880637-82-1 |
352.34 |
25g |
(S)-2-Azido-3-[(9-fluorenylmethyloxycarbonyl)amino]propanoic acid |
| HAA2145.0001 |
N3-D-Dap(Fmoc)-OH |
C18H16N4O4 |
1807631-13-5 |
352.34 |
1g |
(R)-2-Azido-3-[(9-fluorenylmethyloxycarbonyl)amino]propanoic acid |
| HAA2145.0005 |
N3-D-Dap(Fmoc)-OH |
C18H16N4O4 |
1807631-13-5 |
352.34 |
5g |
(R)-2-Azido-3-[(9-fluorenylmethyloxycarbonyl)amino]propanoic acid |
| HAA2145.0025 |
N3-D-Dap(Fmoc)-OH |
C18H16N4O4 |
1807631-13-5 |
352.34 |
25g |
(R)-2-Azido-3-[(9-fluorenylmethyloxycarbonyl)amino]propanoic acid |
| HAA2150.0001 |
N3-L-Dab(Boc)-OH |
C9H16N4O4 |
- |
244.25 |
1g |
(S)-2-Azido-4-((t-butyloxycarbonyl)amino)butanoic acid |
| HAA2150.0005 |
N3-L-Dab(Boc)-OH |
C9H16N4O4 |
- |
244.25 |
5g |
(S)-2-Azido-4-((t-butyloxycarbonyl)amino)butanoic acid |
| HAA2150.0025 |
N3-L-Dab(Boc)-OH |
C9H16N4O4 |
- |
244.25 |
25g |
(S)-2-Azido-4-((t-butyloxycarbonyl)amino)butanoic acid |
| HAA2155.0001 |
N3-D-Dab(Boc)-OH |
C9H16N4O4 |
- |
244.25 |
1g |
(R)-2-Azido-4-((t-butyloxycarbonyl)amino)butanoic acid |
| HAA2155.0005 |
N3-D-Dab(Boc)-OH |
C9H16N4O4 |
- |
244.25 |
5g |
(R)-2-Azido-4-((t-butyloxycarbonyl)amino)butanoic acid |
| HAA2155.0025 |
N3-D-Dab(Boc)-OH |
C9H16N4O4 |
- |
244.25 |
25g |
(R)-2-Azido-4-((t-butyloxycarbonyl)amino)butanoic acid |
| HAA2160.0001 |
N3-L-Lys(Fmoc)-OH |
C21H22N4O4 |
473430-12-5 |
394.42 |
1g |
(S)-2-Azido-6-[(9-fluorenylmethyloxycarbonyl)amino]hexanoic acid |
| HAA2160.0005 |
N3-L-Lys(Fmoc)-OH |
C21H22N4O4 |
473430-12-5 |
394.42 |
5g |
(S)-2-Azido-6-[(9-fluorenylmethyloxycarbonyl)amino]hexanoic acid |
| HAA2160.0025 |
N3-L-Lys(Fmoc)-OH |
C21H22N4O4 |
473430-12-5 |
394.42 |
25g |
(S)-2-Azido-6-[(9-fluorenylmethyloxycarbonyl)amino]hexanoic acid |
| HAA2165.0001 |
N3-D-Lys(Fmoc)-OH |
C21H22N4O4 |
- |
394.42 |
1g |
(R)-2-Azido-3-[(9-fluorenylmethyloxycarbonyl)amino]propanoic acid |
| HAA2165.0005 |
N3-D-Lys(Fmoc)-OH |
C21H22N4O4 |
- |
394.42 |
5g |
(R)-2-Azido-3-[(9-fluorenylmethyloxycarbonyl)amino]propanoic acid |
| HAA2165.0025 |
N3-D-Lys(Fmoc)-OH |
C21H22N4O4 |
- |
394.42 |
25g |
(R)-2-Azido-3-[(9-fluorenylmethyloxycarbonyl)amino]propanoic acid |
| HAA2170.0001 |
N3-L-Lys(Boc)-OH |
C11H20N4O4 |
333366-32-8 |
272.3 |
1g |
(S)-2-Azido-6-[(t-butyloxycarbonyl)amino]hexanoic acid |
| HAA2170.0005 |
N3-L-Lys(Boc)-OH |
C11H20N4O4 |
333366-32-8 |
272.3 |
5g |
(S)-2-Azido-6-[(t-butyloxycarbonyl)amino]hexanoic acid |
| HAA2170.0025 |
N3-L-Lys(Boc)-OH |
C11H20N4O4 |
333366-32-8 |
272.3 |
25g |
(S)-2-Azido-6-[(t-butyloxycarbonyl)amino]hexanoic acid |
| HAA2175.0001 |
N3-D-Lys(Boc)-OH |
C11H20N4O4 |
1178899-92-7 |
272.3 |
1g |
(R)-2-Azido-6-[(t-butyloxycarbonyl)amino]hexanoic acid |
| HAA2175.0005 |
N3-D-Lys(Boc)-OH |
C11H20N4O4 |
1178899-92-7 |
272.3 |
5g |
(R)-2-Azido-6-[(t-butyloxycarbonyl)amino]hexanoic acid |
| HAA2175.0025 |
N3-D-Lys(Boc)-OH |
C11H20N4O4 |
1178899-92-7 |
272.3 |
25g |
(R)-2-Azido-6-[(t-butyloxycarbonyl)amino]hexanoic acid |
| HAA2210.0001 |
N3-D-Orn(Boc)-OH*CHA |
C10H18N4O4*C6H13N |
- |
258,27*99,18 |
1g |
(R)-2-Azido-5-[(t-butyloxycarbonyl)amino]pentanoic acid cyclohexylamine |
| HAA2210.0005 |
N3-D-Orn(Boc)-OH*CHA |
C10H18N4O4*C6H13N |
- |
258,27*99,18 |
5g |
(R)-2-Azido-5-[(t-butyloxycarbonyl)amino]pentanoic acid cyclohexylamine |
| HAA2210.0025 |
N3-D-Orn(Boc)-OH*CHA |
C10H18N4O4*C6H13N |
- |
258,27*99,18 |
25g |
(R)-2-Azido-5-[(t-butyloxycarbonyl)amino]pentanoic acid cyclohexylamine |
| HAA2215.0001 |
N3-D-Orn(Fmoc)-OH |
C20H20N4O4 |
- |
380.4 |
1g |
(R)-2-Azido-5-[(9-fluorenylmethyloxycarbonyl)amino]pentanoic acid |
| HAA2215.0005 |
N3-D-Orn(Fmoc)-OH |
C20H20N4O4 |
- |
380.4 |
5g |
(R)-2-Azido-5-[(9-fluorenylmethyloxycarbonyl)amino]pentanoic acid |
| HAA2215.0025 |
N3-D-Orn(Fmoc)-OH |
C20H20N4O4 |
- |
380.4 |
25g |
(R)-2-Azido-5-[(9-fluorenylmethyloxycarbonyl)amino]pentanoic acid |
| HAA2220.0001 |
N3-L-Orn(Boc)-OH*CHA |
C10H18N4O4*C6H13N |
1639198-67-6 |
258,27*99,18 |
1g |
(S)-2-Azido-5-[(t-butyloxycarbonyl)amino]pentanoic acid cyclohexylamine |
| HAA2220.0005 |
N3-L-Orn(Boc)-OH*CHA |
C10H18N4O4*C6H13N |
1639198-67-6 |
258,27*99,18 |
5g |
(S)-2-Azido-5-[(t-butyloxycarbonyl)amino]pentanoic acid cyclohexylamine |
| HAA2220.0025 |
N3-L-Orn(Boc)-OH*CHA |
C10H18N4O4*C6H13N |
1639198-67-6 |
258,27*99,18 |
25g |
(S)-2-Azido-5-[(t-butyloxycarbonyl)amino]pentanoic acid cyclohexylamine |
| HAA2225.0001 |
N3-L-Orn(Fmoc)-OH |
C20H20N4O4 |
- |
380.4 |
1g |
(S)-2-Azido-5-[(9-fluorenylmethyloxycarbonyl)amino]pentanoic acid |
| HAA2225.0005 |
N3-L-Orn(Fmoc)-OH |
C20H20N4O4 |
- |
380.4 |
5g |
(S)-2-Azido-5-[(9-fluorenylmethyloxycarbonyl)amino]pentanoic acid |
| HAA2225.0025 |
N3-L-Orn(Fmoc)-OH |
C20H20N4O4 |
- |
380.4 |
25g |
(S)-2-Azido-5-[(9-fluorenylmethyloxycarbonyl)amino]pentanoic acid |
| HAA2230.0001 |
N3-1,4-cis-CHC-OH |
C7H11N3O |
863222-21-3 |
169.18 |
1g |
cis-4-Azidocyclohexanecarboxylic acid |
| HAA2230.0005 |
N3-1,4-cis-CHC-OH |
C7H11N3O |
863222-21-3 |
169.18 |
5g |
cis-4-Azidocyclohexanecarboxylic acid |
| HAA2230.0025 |
N3-1,4-cis-CHC-OH |
C7H11N3O |
863222-21-3 |
169.18 |
25g |
cis-4-Azidocyclohexanecarboxylic acid |
| HAA2235.0001 |
N3-1,4-trans-CHC-OH |
C7H11N3O2 |
- |
169.18 |
1g |
trans-4-Azidocyclohexanecarboxylic acid |
| HAA2235.0005 |
N3-1,4-trans-CHC-OH |
C7H11N3O2 |
- |
169.18 |
5g |
trans-4-Azidocyclohexanecarboxylic acid |
| HAA2235.0025 |
N3-1,4-trans-CHC-OH |
C7H11N3O2 |
- |
169.18 |
25g |
trans-4-Azidocyclohexanecarboxylic acid |
| HAA2240.0001 |
N3-trans-MCHC-OH |
C8H13N3O2 |
- |
183.21 |
1g |
trans-4-(Azidomethyl)cyclohexanecarboxylic acid |
| HAA2240.0005 |
N3-trans-MCHC-OH |
C8H13N3O2 |
- |
183.21 |
5g |
trans-4-(Azidomethyl)cyclohexanecarboxylic acid |
| HAA2240.0025 |
N3-trans-MCHC-OH |
C8H13N3O2 |
- |
183.21 |
25g |
trans-4-(Azidomethyl)cyclohexanecarboxylic acid |
| HAA2255.0100 |
N3-Cystamine-Suc-OSu |
C12H17N5O5S2 |
- |
375.42 |
100mg |
4-(2-((2-Azidoethyl)disulfanyl)ethylamino)-4-oxobutanoic acid succinimidyl ester |
| HAA2255.0250 |
N3-Cystamine-Suc-OSu |
C12H17N5O5S2 |
- |
375.42 |
250mg |
4-(2-((2-Azidoethyl)disulfanyl)ethylamino)-4-oxobutanoic acid succinimidyl ester |
| HAA2255.0500 |
N3-Cystamine-Suc-OSu |
C12H17N5O5S2 |
- |
375.42 |
500mg |
4-(2-((2-Azidoethyl)disulfanyl)ethylamino)-4-oxobutanoic acid succinimidyl ester |
| HAA2255.1000 |
N3-Cystamine-Suc-OSu |
C12H17N5O5S2 |
- |
375.42 |
1g |
4-(2-((2-Azidoethyl)disulfanyl)ethylamino)-4-oxobutanoic acid succinimidyl ester |
| HAA2280.0250 |
N3-L-Dbu(Boc)-OH |
C9H16N4O4 |
- |
244.25 |
250mg |
(R)-3-Azido-4-((t-butyloxycarbonyl)amino)butanoic acid |
| HAA2280.1000 |
N3-L-Dbu(Boc)-OH |
C9H16N4O4 |
- |
244.25 |
1g |
(R)-3-Azido-4-((t-butyloxycarbonyl)amino)butanoic acid |
| HAA2280.5000 |
N3-L-Dbu(Boc)-OH |
C9H16N4O4 |
- |
244.25 |
5g |
(R)-3-Azido-4-((t-butyloxycarbonyl)amino)butanoic acid |
| PEG1935.0001 |
Propargyl-NHS |
C10H11NO5 |
1174157-65-3 |
225.2 |
1g |
3-(Prop-2-ynyloxy)propanoic acid succinimidyl ester |
| PEG1935.0100 |
Propargyl-NHS |
C10H11NO5 |
1174157-65-3 |
225.2 |
100mg |
3-(Prop-2-ynyloxy)propanoic acid succinimidyl ester |
| RL-2055.0100 |
Alkyne-myristic acid |
C14H24O2 |
82909-47-5 |
224.34 |
100mg |
13-Tetradecynoic acid |
| RL-2055.0500 |
Alkyne-myristic acid |
C14H24O2 |
82909-47-5 |
224.34 |
500mg |
13-Tetradecynoic acid |
| RL-2055.1000 |
Alkyne-myristic acid |
C14H24O2 |
82909-47-5 |
224.34 |
1g |
13-Tetradecynoic acid |
| RL-2060.0100 |
Alkyne-palmitic acid |
C16H28O2 |
99208-90-9 |
252.39 |
100mg |
15-Hexadecynoic acid |
| RL-2060.0500 |
Alkyne-palmitic acid |
C16H28O2 |
99208-90-9 |
252.39 |
500mg |
15-Hexadecynoic acid |
| RL-2060.1000 |
Alkyne-palmitic acid |
C16H28O2 |
99208-90-9 |
252.39 |
1g |
15-Hexadecynoic acid |
| RL-2065.0100 |
Alkyne-stearic acid |
C18H32O2 |
34450-18-5 |
280.45 |
100mg |
17-Octadecynoic acid |
| RL-2065.0500 |
Alkyne-stearic acid |
C18H32O2 |
34450-18-5 |
280.45 |
500mg |
17-Octadecynoic acid |
| RL-2065.1000 |
Alkyne-stearic acid |
C18H32O2 |
34450-18-5 |
280.45 |
1g |
17-Octadecynoic acid |