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Bioconjugate Chemistry
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(15) Dirksen, A., and Dawson, P. E. (2008) Rapid oxime and
hydrazone ligations with aromatic aldehydes for biomolecular
labeling. Bioconjugate Chem. 19, 2543–2548.
(16) Dirksen, A., Hackeng, T. M., and Dawson, P. E. (2006)
Nucleophilic catalysis of oxime ligation. Angew. Chem., Int. Ed.
45, 7581–7584.
ACKNOWLEDGMENT
Dedicated to Professor Jin-Pei Cheng on the occasion of his
70th birthday. This work was supported by the National
Basic Research Program of China (973 program, Grant Nos.
2013CB911104, 2013CB911100), the National Natural Science
Foundation of China (Grant No. 21572116), and the
Fundamental Research Funds for the Central Universities
(Grant No. 20141081129).
(17) Liu, C.-F., and Tam, J. P. (1994) Chemical ligation approach
to form a peptide bond between unprotected peptide segments.
Concept and model study. J. Am. Chem. Soc. 116, 4149–4153.
(18) Sasaki, T., Kodama, K., Suzuki, H., Fukuzawa, S., and
Tachibana, K. (2008) N-terminal labeling of proteins by the
Pictet–Spengler reaction. Bioorg. Med. Chem. Lett. 18, 4550–4553.
(19) Agarwal, P., van der Weijden, J., Sletten, E. M., Rabuka, D.,
and Bertozzi, C. R. (2013) A Pictet-Spengler ligation for protein
chemical modification. Proc. Natl. Acad. Sci. U. S. A. 110, 46–51.
(20) Han, M.-J., Xiong, D.-C., and Ye, X.-S. (2012) Enabling
wittig reaction on site-specific protein modification. Chem.
Commun. 48, 11079–11081.
(21) Alam, J., Keller, T. H., and Loh, T.-P. (2010)
Functionalization of peptides and proteins by Mukaiyama aldol
reaction. J. Am. Chem. Soc. 132, 9546–9548.
(22) Wang, P., Zhang, S., Meng, Q., Liu, Y., Shang, L., and Yin, Z.
(2015) Site-specific chemical modification of peptide and protein
by thiazolidinediones. Org. Lett. 17, 1361–1364.
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ABBREVIATIONS
ABAO, 2-amino benzamidoxime; TFA, trifluoroacetic acid;
DTT, dithiothreitol; TCEP, Tris(2-carboxyethyl)phosphine;
Boc, tert-butyloxycarbonyl.
REFERENCES
(1) Shieh, P., and Bertozzi, C. R. (2014) Design strategies for
bioorthogonal smart probes. Org. Biomol. Chem. 12, 9307–9320.
(2) Borrmann, A., and van Hest, J. C. M. (2014) Bioorthogonal
chemistry in living organisms. Chem. Sci. 5, 2123–2134.
(3) Spicer, C. D., and Davis, B. G. (2014) Selective chemical
protein modification. Nat. Commun. 5, 4740.
(4) Prescher, J. A., and Bertozzi, C. R. (2005) Chemistry in
living systems. Nat. Chem. Biol. 1, 13–21.
(23) de Almeida, G., Sletten, E. M., Nakamura, H., Palaniappan,
K. K., and Bertozzi, C. R. (2012) Thiacycloalkynes for copper-free
click chemistry. Angew. Chem., Int. Ed. 51, 2443–2447.
(5) Elliott, T. S., Bianco, A., and Chin, J. W. (2014) Genetic
code expansion and bioorthogonal labelling enables cell specific
proteomics in an animal. Curr. Opin. Chem. Biol. 21, 154–160.
(6) Wang, Z., Ding, X., Li, S., Shi, J., and Li, Y. (2014)
Engineered fluorescence tags for in vivo protein labelling. RSC
Adv. 4, 7235–7245.
(7) Li, Y., Yang, M., Huang, Y., Song, X., Liu, L., and Chen, P. R.
(2012) Genetically encoded alkenyl–pyrrolysine analogues for
thiol–ene reaction mediated site-specific protein labeling. Chem.
Sci. 3, 2766–2770.
(8) Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click
chemistry: diverse chemical function from a few good reactions.
Angew. Chem., Int. Ed. 40, 2004–2021.
(9) Carrico, I. S., Carlson, B. L., and Bertozzi, C. R. (2007)
Introducing genetically encoded aldehydes into proteins. Nat.
Chem. Biol. 3, 321–322.
(10) Tuley, A., Lee, Y.-J., Wu, B., Wang, Z. U., and Liu, W. R.
(2014) A genetically encoded aldehyde for rapid protein labelling.
Chem. Commun. 50, 7424–7426.
(11) El-Mahdi, O., and Melnyk, O. (2013) α-oxo aldehyde or
glyoxylyl group chemistry in peptide bioconjugation.
Bioconjugate Chem. 24, 735–765.
(12) Bi, X., Pasunooti, K. K., Lescar, J., and Liu, C.-F. (2017)
Thiazolidine-masked α-oxo aldehyde functionality for peptide
and protein modification. Bioconjugate Chem. 28, 325–329.
(13) Gilmore, J. M., Scheck, R. A., Esser-Kahn, A. P., Joshi, N. S.,
and Francis, M. B. (2006) N-terminal protein modification
through a biomimetic transamination reaction. Angew. Chem.,
Int. Ed. 45, 5307–5311.
(14) Spears, R. J., and Fascione, M. A. (2016) Site-selective
incorporation and ligation of protein aldehydes. Org. Biomol.
Chem. 14, 7622–7638.
(24) Kitov, P. I., Vinals, D. F., Ng, S., Tjhung, K. F., and Derda, R.
(2014)
Rapid,
hydrolytically
stable
modification
of
aldehyde-terminated proteins and phage libraries. J. Am. Chem.
Soc. 136, 8149–8152.
(25) Kudirka, R., Robyn, M. B., McFarland, J., Aaron, E. A.,
Gregory, W. H., Drake, Penelope, M., Patrick, G. H., Banas, S.,
Lesley, C. J., Albert, W. G., et al. (2015) Generating
site-specifically modified proteins via a versatile and stable
nucleophilic carbon ligation. Chem. Biol. 22, 293–298.
(26) Kudirka, R. A., Barfield, R. M., McFarland, J. M., Drake, P.
M., Carlson, A., Bañas, S., Zmolek, W., Garofalo, A. W., and
Rabuka, D. (2016) Site-specific tandem knoevenagel
condensation–michael addition to generate antibody–drug
conjugates. ACS Med. Chem. Lett. 7, 994–998.
(27) Ruan, Q., Ji, Q. C., Arnold, M. E., Humphreys, W. G., and
Zhu, M. (2011) Strategy and its implications of protein bioanalysis
utilizing high-resolution mass spectrometric detection of intact
protein. Anal. Chem. 83, 8937–8944.
(28) Rao, H. S. P., Padmavathy, K., Vasantham, K., and Rafi, S.
(2009) Novel synthesis of methyl ketones based on the blaise
reaction. Synth. Commun. 39, 1825–1834.
(29) Lang, K., and Chin, J. W. (2014) Bioorthogonal reactions for
labeling proteins. ACS Chem. Biol. 9, 16–20.
(30) Patterson, D. M., Nazarova, L. A., and Prescher, J. A. (2014)
Finding the right (bioorthogonal) chemistry. ACS Chem. Biol. 9,
592–605.
(31) Zeng, Y., Ramya, T. N. C., Dirksen, A., Dawson, P. E., and
Paulson, J. C. (2009) High-efficiency labeling of sialylated
glycoproteins on living cells. Nat. Methods 6, 207–209.
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