二氮雜環丙烯

3H-二氮雜環丙烯
英文名	3H-Diazirine
別名	二氮雜丙(熳)環; 雙吖丙啶
識別
CAS號	157-22-2
PubChem	78958
ChemSpider	71291
SMILES	C1N=N1;
Beilstein	605387
ChEBI	51620
性質
化學式	CH2N2
摩爾質量	42.04 g·mol−1
相關物質
相關化學品	1H-Diazirene
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

3H-二氮雜環丙烯（英語：3H-Diazirine）是一種含氮的雜環有機化合物，分子式為CH₂N₂，分子中氮原子以雙鍵連接，形成類似環丙烯的結構。二氮雜環丙烯^{[註 1]}有一個分子中氮以單鍵連接的同分異構體。

Quick Facts 3H-二氮雜環丙烯, 識別 ...

Close

3H-二氮雜環丙烯可以作為卡賓的前體，例如用紫外線照射二氮雜環丙烯能使之分解為氮氣和對應卡賓^[1]。因此，二氮雜環丙烯作為小型光反應性交聯劑越來越受歡迎^[2]。經常被用於光親和標記（英語：photoaffinity labeling）研究，來觀察各種相互作用，包括配體-受體、配體-酶、蛋白質-蛋白質和蛋白質-核酸間的相互作用^[3]。

合成

酮合成

由酮合成二氮雜環丙烯，通常先由對應酮與羥胺在鹼性存在（如吡啶）下，加入鹽酸羥胺加熱肟化^[4]^[5]，在鹼與對甲苯磺酰氯的作用下發生Neber重排反應,最後用氨處理得到二氮雜環丙烯結構^[1]^[3]^[6]^[7]。

二氮雜環丙烯也可以直接由酮與氨和氯胺作用下直接得到二氮雜環丙烷，再利用氧化銀氧化得到二氮雜環丙烯^[8]^[9]。二氮雜環丙烯可以由多種氧化劑氧化二氮雜環丙烷結構而來，例如Jones氧化 ^[10]、碘和三乙胺氧化^[4] 、氧化銀氧化^[11]、草酰氯氧化^[6]、鉑鈦電極電化學氧化^[12]。

脒合成

由脒合成二氮雜環丙烯，該反應稱為Graham反應（英語：Graham reaction），可以一鍋法合成鹵代二氮雜環丙烯^[13]，其上的鹵原子可以被親核試劑取代^[14]。

Graham反應使用次鹵酸鈉氧化脒合成二氮雜環丙烯。

使用抗衡離子四丁基銨鹽（英語：tetrabutylammonium）和親核離子可以取代其上鹵原子。

化學研究

用紫外線輻照後，二氮雜環丙烯會產生單線態或三線態的對應卡賓。

二氮雜環丙烯上的取代基會影響其光解後生成卡賓電子的分佈狀態，二氮雜環丙烯環可以向卡賓碳空p軌道中提供電子，因此得到單線態卡賓分子。例如：苯基二氮雜環丙烯產生的卡賓是單線態的^[15]，而三氟甲基苯基二氮雜環丙烯與對硝基苯基二氮雜環丙烯產生的卡賓是三線態的^[16]^[17]。

除了分解為卡賓外，給電子取代基會引發光異構化反應使二氮雜環丙烯環異構為線性的重氮結構，而此類物質不適合用於生物學化驗^[18]。相對的，三氟甲基芳基二氮雜環丙烯表現出良好的化學穩定性和光解卡賓產率^[18]，能廣泛用於生物學研究^[1]。

二氮雜環丙烯產生的卡賓遇水會快速淬滅 ^[19]，因此光反應性交聯實驗的產率通常很低。然而，由此大量減少的非特異性標記也是使用二氮雜環丙烯的一個優勢。

生物研究

二氮雜環丙烯可以用作光反應性交聯劑，光解產生的卡賓可以插入C-H、N-H和O-H鍵，實現其他物質與二氮雜環丙烯環的鄰近依賴性標記（英語：proximity labeling）。由於二氮雜環丙烯擁有較小的體積、較長的輻射波長、短輻照時間、對酸鹼穩定的優點，是最常用的光反應性交聯劑^[20]。

二苯甲酮在長時間輻照後產生三線態卡賓，可能會產生許多非特異性標記，而且通常對各種極性溶劑呈化學惰性^[21]。芳基疊氮化物則需要低波長的輻照，可能會破壞目標生物大分子。

受體標記研究

二氮雜環丙烯可以合成含各種配體的類似物並與對應受體一同孵育，然後光解產生對應卡賓，卡賓將與特徵受體結合點的共價殘基結合。該卡賓化合物包括生物正交標記或處理，並以此分離感興趣的蛋白質。通過質譜對蛋白質進行消化和測序，鑑定卡賓與哪些殘基結合，來確定受體中的結合點位。

受體標記研究中使用二氮雜環丙烯的例子有：

Kinoshita等人通過使用含二氮雜環丙烯交聯結構和生物素標籤的植物激素類似物進行分離，發現了油菜素類固醇植物激素的油菜素類固醇受體，並推動了類似的其他植物激素研究^[22]。

Balas等人^[23]通過含二氮雜環丙烯結構的花生四烯酸乙醇胺類似物探針發現了新型非CB1/CB2大麻素受體。

安眠藥丙泊酚在GABA_A受體鍵合腔內使用含二氮雜環丙烯結構的丙泊酚類似物^[24]。

丙泊酚 (左) 與其類似物m-Azipropofol

酶底物研究

類似於受體標記的方法，含有二氮雜環丙烯的天然底物類似物可用於判定酶的鍵合口袋，例如：

合成含有二氮雜環丙烯結構的依託泊苷類似物，一種被廣泛使用的靶向二型拓撲異構酶，被寄望用於尋找依託泊苷的結合位點 ^[25]。

核酸研究

二氮雜環丙烯也被用於涉及核酸的光親核標記實驗，例如：

DNA聚合物中的核苷酸糖上結合二氮雜環丙烯結構來研究DNA小溝和DNA聚合酶間的相互作用^[26]。

DNA聚合物中的核苷酸鹼基上結合二氮雜環丙烯結構來研究蛋白質修復DNA的模式^[27]。

二氮雜環丙烯被用於研究蛋白質脂質相互作用，例如鞘脂和體內蛋白質的相互作用。

備註

[註 1]
下文如無註明，則均以二氮雜環丙烯指代3H-diazirine

參見

參考文獻

[1]
Dubinsky, Luba; Krom, Bastiaan P.; Meijler, Michael M. Diazirine based photoaffinity labeling. Bioorganic & Medicinal Chemistry. Chemical Proteomics. 2012-01-15, 20 (2): 554–570. PMID 21778062. doi:10.1016/j.bmc.2011.06.066.
[2]
Hill, James R.; Robertson, Avril A. B. Fishing for Drug Targets: A Focus on Diazirine Photoaffinity Probe Synthesis. Journal of Medicinal Chemistry. 2018, 61 (16): 6945–6963 [2021-12-06]. PMID 29683660. doi:10.1021/acs.jmedchem.7b01561. （原始內容存檔於2021-12-06）.
[3]
Sinz, Andrea. Investigation of protein-ligand interactions by mass spectrometry. ChemMedChem. 2007-04-01, 2 (4): 425–431. ISSN 1860-7187. PMID 17299828. S2CID 23769515. doi:10.1002/cmdc.200600298.
[4]
Burkard, Nadja; Bender, Tobias; Westmeier, Johannes; Nardmann, Christin; Huss, Markus; Wieczorek, Helmut; Grond, Stephanie; von Zezschwitz, Paultheo. New Fluorous Photoaffinity Labels (F-PAL) and Their Application in V-ATPase Inhibition Studies. European Journal of Organic Chemistry. 2010-04-01, 2010 (11): 2176–2181. ISSN 1099-0690. doi:10.1002/ejoc.200901463.
[5]
Song, Zhiquan; Zhang, Qisheng. Fluorous Aryldiazirine Photoaffinity Labeling Reagents. Organic Letters. 2009-11-05, 11 (21): 4882–4885. ISSN 1523-7060. PMID 19807115. doi:10.1021/ol901955y.
[6]
Kumar, Nag S.; Young, Robert N. Design and synthesis of an all-in-one 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group for photo-affinity labeling. Bioorganic & Medicinal Chemistry. 2009-08-01, 17 (15): 5388–5395. PMID 19604700. doi:10.1016/j.bmc.2009.06.048.
[7]
Gu, Min; Yan, Jianbin; Bai, Zhiyan; Chen, Yue-Ting; Lu, Wei; Tang, Jie; Duan, Liusheng; Xie, Daoxin; Nan, Fa-Jun. Design and synthesis of biotin-tagged photoaffinity probes of jasmonates. Bioorganic & Medicinal Chemistry. 2010-05-01, 18 (9): 3012–3019. PMID 20395151. doi:10.1016/j.bmc.2010.03.059.
[8]
Dubinsky, Luba; Jarosz, Lucja M.; Amara, Neri; Krief, Pnina; Kravchenko, Vladimir V.; Krom, Bastiaan P.; Meijler, Michael M. Synthesis and validation of a probe to identify quorum sensing receptors. Chemical Communications. 2009-11-24, (47): 7378–7380. PMID 20024234. doi:10.1039/b917507e.
[9]
Vishnu Ji Ram; Arun Sethi; Mahendra Nath; Ramendra Pratap. The Chemistry of Heterocycles. Elsevier. 2019: 19-92. ISBN 9780081010334.
[10]
Wagner, Gerald; Knoll, Wolfgang; Bobek, Michael M.; Brecker, Lothar; van Herwijnen, Hendrikus W. G.; Brinker, Udo H. Structure−Reactivity Relationships: Reactions of a 5-Substituted Aziadamantane in a Resorcin[4]arene-based Cavitand. Organic Letters. 2010-01-15, 12 (2): 332–335. ISSN 1523-7060. PMID 20017550. doi:10.1021/ol902667a.
[11]
Al-Omari, Mohammad; Banert, Klaus; Hagedorn, Manfred. Bi-3H-diazirin-3-yls as Precursors of Highly Strained Cycloalkynes. Angewandte Chemie International Edition. 2006-01-01, 45 (2): 309–311. ISSN 1521-3773. PMID 16372311. doi:10.1002/anie.200503124.
[12]
Vedenyapina, M. D.; Kuznetsov, V. V.; Nizhnikovskii, E. A.; Strel’tsova, E. D.; Makhova, N. N.; Struchkova, M. I.; Vedenyapin, A. A. Electrochemical synthesis of pentamethylenediazirine. Russian Chemical Bulletin. 2006-11-01, 55 (11): 2013–2015. ISSN 1066-5285. S2CID 97472127. doi:10.1007/s11172-006-0544-0.
[13]
Graham, W. H. The Halogenation of Amidines. I. Synthesis of 3-Halo- and Other Negatively Substituted Diazirines1. Journal of the American Chemical Society. 1965-10-01, 87 (19): 4396–4397. ISSN 0002-7863. doi:10.1021/ja00947a040.
[14]
Moss, Robert A. Diazirines: Carbene Precursors Par Excellence. Accounts of Chemical Research. 2006-02-09, 39 (4): 267–272. ISSN 0001-4842. PMID 16618094. doi:10.1021/ar050155h.
[15]
Zhang, Yunlong; Burdzinski, Gotard; Kubicki, Jacek; Platz, Matthew S. Direct Observation of Carbene and Diazo Formation from Aryldiazirines by Ultrafast Infrared Spectroscopy. Journal of the American Chemical Society. 2008-12-03, 130 (48): 16134–16135. ISSN 0002-7863. PMID 18998681. doi:10.1021/ja805922b.
[16]
Noller, Bastian; Poisson, Lionel; Maksimenka, Raman; Gobert, Oliver; Fischer, Ingo; Mestdagh, J. M. Ultrafast Dynamics of Isolated Phenylcarbenes Followed by Femtosecond Time-Resolved Velocity Map Imaging. The Journal of Physical Chemistry A. 2009-04-02, 113 (13): 3041–3050. Bibcode:2009JPCA..113.3041N. ISSN 1089-5639. PMID 19245233. doi:10.1021/jp810974m.
[17]
Noller, Bastian; Hemberger, Patrick; Fischer, Ingo; Alcaraz, Christian; Garcia, Gustavo A.; Soldi-Lose, Héloïse. The photoionisation of two phenylcarbenes and their diazirine precursors investigated using synchrotron radiation. Physical Chemistry Chemical Physics. 2009-06-23, 11 (26): 5384–5391 [2021-12-06]. Bibcode:2009PCCP...11.5384N. PMID 19551206. doi:10.1039/b823269e. （原始內容存檔於2021-12-06）.
[18]
Brunner, J.; Senn, H.; Richards, F. M. 3-Trifluoromethyl-3-phenyldiazirine. A new carbene generating group for photolabeling reagents. The Journal of Biological Chemistry. 1980-04-25, 255 (8): 3313–3318. ISSN 0021-9258. PMID 7364745. doi:10.1016/S0021-9258(19)85701-0 .
[19]
Wang, Jin; Kubicki, Jacek; Peng, Huolei; Platz, Matthew S. Influence of Solvent on Carbene Intersystem Crossing Rates. Journal of the American Chemical Society. 2008-05-01, 130 (20): 6604–6609. ISSN 0002-7863. PMID 18433130. doi:10.1021/ja711385t.
[20]
Hatanaka, Yasumaru; Sadakane, Yutaka. Photoaffinity labeling in drug discovery and developments: chemical gateway for entering proteomic frontier. Current Topics in Medicinal Chemistry. 2002-03-01, 2 (3): 271–288. ISSN 1568-0266. PMID 11944820. doi:10.2174/1568026023394182.
[21]
Prestwich, Glenn D.; Dormán, György; Elliott, John T.; Marecak, Dale M.; Chaudhary, Anu. Benzophenone Photoprobes for Phosphoinositides, Peptides and Drugs. Photochemistry and Photobiology. 1997-02-01, 65 (2): 222–234. ISSN 1751-1097. PMID 9066302. S2CID 12577596. doi:10.1111/j.1751-1097.1997.tb08548.x.
[22]
Kinoshita, Toshinori; Caño-Delgado, Ana; Seto, Hideharu; Hiranuma, Sayoko; Fujioka, Shozo; Yoshida, Shigeo; Chory, Joanne. Binding of brassinosteroids to the extracellular domain of plant receptor kinase BRI1. Nature. 2005, 433 (7022): 167–171. Bibcode:2005Natur.433..167K. PMID 15650741. S2CID 4379617. doi:10.1038/nature03227.
[23]
Balas, Laurence; Durand, Thierry; Saha, Sattyabrata; Johnson, Inneke; Mukhopadhyay, Somnath. Total Synthesis of Photoactivatable or Fluorescent Anandamide Probes: Novel Bioactive Compounds with Angiogenic Activity. Journal of Medicinal Chemistry. 2009-02-26, 52 (4): 1005–1017. ISSN 0022-2623. PMID 19161308. doi:10.1021/jm8011382.
[24]
Hall, Michael A.; Xi, Jin; Lor, Chong; Dai, Shuiping; Pearce, Robert; Dailey, William P.; Eckenhoff, Roderic G. m-Azipropofol (AziPm) a Photoactive Analogue of the Intravenous General Anesthetic Propofol. Journal of Medicinal Chemistry. 2010-08-12, 53 (15): 5667–5675. ISSN 0022-2623. PMC 2917171 . PMID 20597506. doi:10.1021/jm1004072.
[25]
Chee, Gaik-Lean; Yalowich, Jack C.; Bodner, Andrew; Wu, Xing; Hasinoff, Brian B. A diazirine-based photoaffinity etoposide probe for labeling topoisomerase II. Bioorganic & Medicinal Chemistry. 2010-01-15, 18 (2): 830–838. PMC 2818565 . PMID 20006518. doi:10.1016/j.bmc.2009.11.048.
[26]
Liebmann, Meike; Di Pasquale, Francesca; Marx, Andreas. A New Photoactive Building Block for Investigation of DNA Backbone Interactions: Photoaffinity Labeling of Human DNA Polymerase β. ChemBioChem. 2006-12-04, 7 (12): 1965–1969. ISSN 1439-7633. PMID 17106908. S2CID 22908416. doi:10.1002/cbic.200600333.
[27]
Winnacker, Malte; Breeger, Sascha; Strasser, Ralf; Carell, Thomas. Novel Diazirine-Containing DNA Photoaffinity Probes for the Investigation of DNA-Protein-Interactions. ChemBioChem. 2009-01-05, 10 (1): 109–118. ISSN 1439-7633. PMID 19012292. S2CID 5605171. doi:10.1002/cbic.200800397.

[1] [註 1]
下文如無註明，則均以二氮雜環丙烯指代3H-diazirine

[:0-2] [1]
Dubinsky, Luba; Krom, Bastiaan P.; Meijler, Michael M. Diazirine based photoaffinity labeling. Bioorganic & Medicinal Chemistry. Chemical Proteomics. 2012-01-15, 20 (2): 554–570. PMID 21778062. doi:10.1016/j.bmc.2011.06.066.

[3] [2]
Hill, James R.; Robertson, Avril A. B. Fishing for Drug Targets: A Focus on Diazirine Photoaffinity Probe Synthesis. Journal of Medicinal Chemistry. 2018, 61 (16): 6945–6963 [2021-12-06]. PMID 29683660. doi:10.1021/acs.jmedchem.7b01561. （原始內容存檔於2021-12-06）.

[:1-4] [3]
Sinz, Andrea. Investigation of protein-ligand interactions by mass spectrometry. ChemMedChem. 2007-04-01, 2 (4): 425–431. ISSN 1860-7187. PMID 17299828. S2CID 23769515. doi:10.1002/cmdc.200600298.

[:2-5] [4]
Burkard, Nadja; Bender, Tobias; Westmeier, Johannes; Nardmann, Christin; Huss, Markus; Wieczorek, Helmut; Grond, Stephanie; von Zezschwitz, Paultheo. New Fluorous Photoaffinity Labels (F-PAL) and Their Application in V-ATPase Inhibition Studies. European Journal of Organic Chemistry. 2010-04-01, 2010 (11): 2176–2181. ISSN 1099-0690. doi:10.1002/ejoc.200901463.

[6] [5]
Song, Zhiquan; Zhang, Qisheng. Fluorous Aryldiazirine Photoaffinity Labeling Reagents. Organic Letters. 2009-11-05, 11 (21): 4882–4885. ISSN 1523-7060. PMID 19807115. doi:10.1021/ol901955y.

[:3-7] [6]
Kumar, Nag S.; Young, Robert N. Design and synthesis of an all-in-one 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group for photo-affinity labeling. Bioorganic & Medicinal Chemistry. 2009-08-01, 17 (15): 5388–5395. PMID 19604700. doi:10.1016/j.bmc.2009.06.048.

[8] [7]
Gu, Min; Yan, Jianbin; Bai, Zhiyan; Chen, Yue-Ting; Lu, Wei; Tang, Jie; Duan, Liusheng; Xie, Daoxin; Nan, Fa-Jun. Design and synthesis of biotin-tagged photoaffinity probes of jasmonates. Bioorganic & Medicinal Chemistry. 2010-05-01, 18 (9): 3012–3019. PMID 20395151. doi:10.1016/j.bmc.2010.03.059.

[9] [8]
Dubinsky, Luba; Jarosz, Lucja M.; Amara, Neri; Krief, Pnina; Kravchenko, Vladimir V.; Krom, Bastiaan P.; Meijler, Michael M. Synthesis and validation of a probe to identify quorum sensing receptors. Chemical Communications. 2009-11-24, (47): 7378–7380. PMID 20024234. doi:10.1039/b917507e.

[H-10] [9]
Vishnu Ji Ram; Arun Sethi; Mahendra Nath; Ramendra Pratap. The Chemistry of Heterocycles. Elsevier. 2019: 19-92. ISBN 9780081010334.

[11] [10]
Wagner, Gerald; Knoll, Wolfgang; Bobek, Michael M.; Brecker, Lothar; van Herwijnen, Hendrikus W. G.; Brinker, Udo H. Structure−Reactivity Relationships: Reactions of a 5-Substituted Aziadamantane in a Resorcin[4]arene-based Cavitand. Organic Letters. 2010-01-15, 12 (2): 332–335. ISSN 1523-7060. PMID 20017550. doi:10.1021/ol902667a.

[12] [11]
Al-Omari, Mohammad; Banert, Klaus; Hagedorn, Manfred. Bi-3H-diazirin-3-yls as Precursors of Highly Strained Cycloalkynes. Angewandte Chemie International Edition. 2006-01-01, 45 (2): 309–311. ISSN 1521-3773. PMID 16372311. doi:10.1002/anie.200503124.

[13] [12]
Vedenyapina, M. D.; Kuznetsov, V. V.; Nizhnikovskii, E. A.; Strel’tsova, E. D.; Makhova, N. N.; Struchkova, M. I.; Vedenyapin, A. A. Electrochemical synthesis of pentamethylenediazirine. Russian Chemical Bulletin. 2006-11-01, 55 (11): 2013–2015. ISSN 1066-5285. S2CID 97472127. doi:10.1007/s11172-006-0544-0.

[14] [13]
Graham, W. H. The Halogenation of Amidines. I. Synthesis of 3-Halo- and Other Negatively Substituted Diazirines1. Journal of the American Chemical Society. 1965-10-01, 87 (19): 4396–4397. ISSN 0002-7863. doi:10.1021/ja00947a040.

[15] [14]
Moss, Robert A. Diazirines: Carbene Precursors Par Excellence. Accounts of Chemical Research. 2006-02-09, 39 (4): 267–272. ISSN 0001-4842. PMID 16618094. doi:10.1021/ar050155h.

[16] [15]
Zhang, Yunlong; Burdzinski, Gotard; Kubicki, Jacek; Platz, Matthew S. Direct Observation of Carbene and Diazo Formation from Aryldiazirines by Ultrafast Infrared Spectroscopy. Journal of the American Chemical Society. 2008-12-03, 130 (48): 16134–16135. ISSN 0002-7863. PMID 18998681. doi:10.1021/ja805922b.

[17] [16]
Noller, Bastian; Poisson, Lionel; Maksimenka, Raman; Gobert, Oliver; Fischer, Ingo; Mestdagh, J. M. Ultrafast Dynamics of Isolated Phenylcarbenes Followed by Femtosecond Time-Resolved Velocity Map Imaging. The Journal of Physical Chemistry A. 2009-04-02, 113 (13): 3041–3050. Bibcode:2009JPCA..113.3041N. ISSN 1089-5639. PMID 19245233. doi:10.1021/jp810974m.

[18] [17]
Noller, Bastian; Hemberger, Patrick; Fischer, Ingo; Alcaraz, Christian; Garcia, Gustavo A.; Soldi-Lose, Héloïse. The photoionisation of two phenylcarbenes and their diazirine precursors investigated using synchrotron radiation. Physical Chemistry Chemical Physics. 2009-06-23, 11 (26): 5384–5391 [2021-12-06]. Bibcode:2009PCCP...11.5384N. PMID 19551206. doi:10.1039/b823269e. （原始內容存檔於2021-12-06）.

[:4-19] [18]
Brunner, J.; Senn, H.; Richards, F. M. 3-Trifluoromethyl-3-phenyldiazirine. A new carbene generating group for photolabeling reagents. The Journal of Biological Chemistry. 1980-04-25, 255 (8): 3313–3318. ISSN 0021-9258. PMID 7364745. doi:10.1016/S0021-9258(19)85701-0 .

[20] [19]
Wang, Jin; Kubicki, Jacek; Peng, Huolei; Platz, Matthew S. Influence of Solvent on Carbene Intersystem Crossing Rates. Journal of the American Chemical Society. 2008-05-01, 130 (20): 6604–6609. ISSN 0002-7863. PMID 18433130. doi:10.1021/ja711385t.

[21] [20]
Hatanaka, Yasumaru; Sadakane, Yutaka. Photoaffinity labeling in drug discovery and developments: chemical gateway for entering proteomic frontier. Current Topics in Medicinal Chemistry. 2002-03-01, 2 (3): 271–288. ISSN 1568-0266. PMID 11944820. doi:10.2174/1568026023394182.

[22] [21]
Prestwich, Glenn D.; Dormán, György; Elliott, John T.; Marecak, Dale M.; Chaudhary, Anu. Benzophenone Photoprobes for Phosphoinositides, Peptides and Drugs. Photochemistry and Photobiology. 1997-02-01, 65 (2): 222–234. ISSN 1751-1097. PMID 9066302. S2CID 12577596. doi:10.1111/j.1751-1097.1997.tb08548.x.

[23] [22]
Kinoshita, Toshinori; Caño-Delgado, Ana; Seto, Hideharu; Hiranuma, Sayoko; Fujioka, Shozo; Yoshida, Shigeo; Chory, Joanne. Binding of brassinosteroids to the extracellular domain of plant receptor kinase BRI1. Nature. 2005, 433 (7022): 167–171. Bibcode:2005Natur.433..167K. PMID 15650741. S2CID 4379617. doi:10.1038/nature03227.

[24] [23]
Balas, Laurence; Durand, Thierry; Saha, Sattyabrata; Johnson, Inneke; Mukhopadhyay, Somnath. Total Synthesis of Photoactivatable or Fluorescent Anandamide Probes: Novel Bioactive Compounds with Angiogenic Activity. Journal of Medicinal Chemistry. 2009-02-26, 52 (4): 1005–1017. ISSN 0022-2623. PMID 19161308. doi:10.1021/jm8011382.

[25] [24]
Hall, Michael A.; Xi, Jin; Lor, Chong; Dai, Shuiping; Pearce, Robert; Dailey, William P.; Eckenhoff, Roderic G. m-Azipropofol (AziPm) a Photoactive Analogue of the Intravenous General Anesthetic Propofol. Journal of Medicinal Chemistry. 2010-08-12, 53 (15): 5667–5675. ISSN 0022-2623. PMC 2917171 . PMID 20597506. doi:10.1021/jm1004072.

[26] [25]
Chee, Gaik-Lean; Yalowich, Jack C.; Bodner, Andrew; Wu, Xing; Hasinoff, Brian B. A diazirine-based photoaffinity etoposide probe for labeling topoisomerase II. Bioorganic & Medicinal Chemistry. 2010-01-15, 18 (2): 830–838. PMC 2818565 . PMID 20006518. doi:10.1016/j.bmc.2009.11.048.

[27] [26]
Liebmann, Meike; Di Pasquale, Francesca; Marx, Andreas. A New Photoactive Building Block for Investigation of DNA Backbone Interactions: Photoaffinity Labeling of Human DNA Polymerase β. ChemBioChem. 2006-12-04, 7 (12): 1965–1969. ISSN 1439-7633. PMID 17106908. S2CID 22908416. doi:10.1002/cbic.200600333.

[28] [27]
Winnacker, Malte; Breeger, Sascha; Strasser, Ralf; Carell, Thomas. Novel Diazirine-Containing DNA Photoaffinity Probes for the Investigation of DNA-Protein-Interactions. ChemBioChem. 2009-01-05, 10 (1): 109–118. ISSN 1439-7633. PMID 19012292. S2CID 5605171. doi:10.1002/cbic.200800397.

[註 1]

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]

[15]

[16]

[17]

[18]

[19]

[20]

[21]

[22]

[23]

[24]

[25]

[26]

[27]