Photocatalyzed elaboration of antibody-based bioconjugates

• Marine Le Stum,
• Eugénie Romero and
• Gary A. Molander

Beilstein J. Org. Chem. 2025, 21, 616–629, doi:10.3762/bjoc.21.49

• ; bioorthogonality; chemoselectivity; late-stage functionalization; photochemistry; Introduction Antibodies represent increasingly important tools in several groundbreaking approaches to medical innovation, including basic biomedical research and therapy. One of the most critical requirements for the application of

• light control might also be improved using photochemical transformations. Importantly, optimization of bioconjugation reactions with technologies such as high-throughput experimentation has already been applied on antibodies [51]. Bioorthogonality Bioorthogonal chemistry has transformed our capability

• attaching multiple payloads to a single antibody molecule with high homogeneity [54][55][56]. Generating homogeneous multi-payload ADCs is complex because of the diverse reactive functional groups on antibody surfaces. As outlined above in the discussion concerning bioorthogonality, it is conceivable that

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

• Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

• , demonstrating significant bioorthogonality in manganese(I) catalysis. The robustness of the method bears significance for further synthetic applications, such as “Click” chemistry or N-functionalization. Moreover, as shown in Scheme 9B, the manganese(I) catalysis regime enabled peptide macrocyclization (see 25f

A postsynthetically 2’-“clickable” uridine with arabino configuration and its application for fluorescent labeling and imaging of DNA

• Heidi-Kristin Walter,
• Bettina Olshausen,
• Ute Schepers and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2017, 13, 127–137, doi:10.3762/bjoc.13.16

• not present in nucleic acids [2][3][4][5]. Although Huisgen described the uncatalyzed reaction yielding 1,2,3-triazoles already in the 1960s [6], the bioorthogonality with respect to proteins and nucleic acids emerged after Sharpless [7] and Meldal [8] had reported that catalysis by Cu(I) enhances not

Bioorthogonal metabolic glycoengineering of human larynx carcinoma (HEp-2) cells targeting sialic acid

• Arne Homann,
• Riaz-ul Qamar,
• Sevnur Serim,
• Petra Dersch and
• Jürgen Seibel

Beilstein J. Org. Chem. 2010, 6, No. 24, doi:10.3762/bjoc.6.24

• Synthesis of the sialic acid analogue N-(1-oxohex-5-ynyl)neuraminic acid (Neu5Hex, 3) The bioorthogonality of N-(1-oxohex-5-ynyl)neuraminic acid (3) was exploited to incorporate it into human larynx carcinoma (HEp-2) cells by metabolic glycoengineering. The synthesis of N-(1-oxohex-5-ynyl)neuraminic acid

• surface presentation of Ac4GlcNAc 16 as well as the new substrate Neu5Hex 3 was successful. The copper-catalyzed [3+2] triazole formation (“click reaction”) proved very useful for the cell surface labelling because of its bioorthogonality. The incubation of HEp-2 cells with the sialic acid analogue

Synthetic incorporation of Nile Blue into DNA using 2′-deoxyriboside substitutes: Representative comparison of (R)- and (S)-aminopropanediol as an acyclic linker

• Daniel Lachmann,
• Sina Berndl,
• Otto S. Wolfbeis and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2010, 6, No. 13, doi:10.3762/bjoc.6.13

• ]. Bioorthogonality is required for these ligation reactions in that both the functional group of the oligonucleotides and the functional group of the modifier should not be present in typical biomolecules and should react selectively with each other [11]. Over the last five years the Huisgen–Meldal–Sharpless “click

• at the same time – Sharpless [16] had reported that the addition of Cu(I) led to a significant increase in the reaction rate and in regioselectivity. This type of “click” chemistry matches the requirements of bioorthogonality since both two functional groups, alkyne and azide, are typically not