Employing Unnatural Amino Acids in the Preparation of Biooconjugates

被引:14
作者
Maza, Johnathan C. [1 ]
Jacobs, Taylor H. [1 ]
Uthappa, Diya M. [1 ]
Young, Douglas D. [1 ]
机构
[1] Coll William & Mary, Dept Chem, POB 8795, Williamsburg, VA 23187 USA
关键词
bioconjugations; unnatural amino acids; cycloadditions; biorthogonal; Glaser-Hay coupling; SITE-SPECIFIC INCORPORATION; COPPER-FREE; BIOORTHOGONAL REACTIONS; PROTEIN; CHEMISTRY; ALKYNE; CYCLOADDITION; ANTIBODIES; BIOCONJUGATION; PEGYLATION;
D O I
10.1055/s-0035-1560551
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The exploitation of unnatural amino acid (UAA) technologies represents an excellent mechanism for the generation of site-specific bioconjugates. Consequently, significant effort has been invested in the advancement of the technology via the integration of novel bioconjugation reactions and the expansion of the set of UAAs that can be employed. Herein, we report the recent developments in the field and highlight advantages and disadvantages of various UAA bioconjugation reactions.
引用
收藏
页码:805 / 813
页数:9
相关论文
共 81 条
[1]   A comparative study of bioorthogonal reactions with azides [J].
Agard, Nicholas J. ;
Baskin, Jeremy M. ;
Prescher, Jennifer A. ;
Lo, Anderson ;
Bertozzi, Carolyn R. .
ACS CHEMICAL BIOLOGY, 2006, 1 (10) :644-648
[2]   A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems [J].
Agard, NJ ;
Prescher, JA ;
Bertozzi, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15046-15047
[3]   Ligand-targeted therapeutics in anticancer therapy [J].
Allen, TM .
NATURE REVIEWS CANCER, 2002, 2 (10) :750-763
[4]   P-MALEIMIDOPHENYL ISOCYANATE - A NOVEL HETEROBIFUNCTIONAL LINKER FOR HYDROXYL TO THIOL COUPLING [J].
ANNUNZIATO, ME ;
PATEL, US ;
RANADE, M ;
PALUMBO, PS .
BIOCONJUGATE CHEMISTRY, 1993, 4 (03) :212-218
[5]   Synthesis of site-specific antibody-drug conjugates using unnatural amino acids [J].
Axup, Jun Y. ;
Bajjuri, Krishna M. ;
Ritland, Melissa ;
Hutchins, Benjamin M. ;
Kim, Chan Hyuk ;
Kazane, Stephanie A. ;
Halder, Rajkumar ;
Forsyth, Jane S. ;
Santidrian, Antonio F. ;
Stafin, Karin ;
Lu, Yingchun ;
Hon Tran ;
Seller, Aaron J. ;
Biroce, Sandra L. ;
Szydlik, Aga ;
Pinkstaff, Jason K. ;
Tian, Feng ;
Sinha, Subhash C. ;
Felding-Habermann, Brunhilde ;
Smider, Vaughn V. ;
Schultz, Peter G. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2012, 109 (40) :16101-16106
[6]   Copper-free click chemistry for dynamic in vivo imaging [J].
Baskin, Jeremy M. ;
Prescher, Jennifer A. ;
Laughlin, Scott T. ;
Agard, Nicholas J. ;
Chang, Pamela V. ;
Miller, Isaac A. ;
Lo, Anderson ;
Codelli, Julian A. ;
Bertozzi, Carolyn R. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) :16793-16797
[7]   Ideal Bioorthogonal Reactions Using A Site-Specifically Encoded Tetrazine Amino Acid [J].
Blizzard, Robert J. ;
Backus, Dakota R. ;
Brown, Wes ;
Bazewicz, Christopher G. ;
Li, Yi ;
Mehl, Ryan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (32) :10044-10047
[8]   Quantum Dot DNA Bioconjugates: Attachment Chemistry Strongly Influences the Resulting Composite Architecture [J].
Boeneman, Kelly ;
Deschamps, Jeffrey R. ;
Buckhout-White, Susan ;
Prasuhn, Duane E. ;
Blanco-Canosa, Juan B. ;
Dawson, Philip E. ;
Stewart, Michael H. ;
Susumu, Kimihiro ;
Goldman, Ellen R. ;
Ancona, Mario ;
Medintz, Igor L. .
ACS NANO, 2010, 4 (12) :7253-7266
[9]   Strain-Promoted Oxidation-Controlled Cyclooctyne-1,2-Quinone Cycloaddition (SPOCQ) for Fast and Activatable Protein Conjugation [J].
Borrmann, Annika ;
Fatunsin, Olumide ;
Dommerholt, Jan ;
Jonker, Anika M. ;
Lowik, Dennis W. P. M. ;
van Hest, Jan C. M. ;
van Delft, Floris L. .
BIOCONJUGATE CHEMISTRY, 2015, 26 (02) :257-261
[10]   A Genetically Encoded Boronate-Containing Amino Acid [J].
Brustad, Eric ;
Bushey, Mark L. ;
Lee, Jae Wook ;
Groff, Dan ;
Liu, Wenshe ;
Schultz, Peter G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (43) :8220-8223