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Please login to access the full content or check if you have access via2.4 On-DNA C—X (X = N, O, P, S, Se) Bond Forming Reactions
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Hou, W.; Yang, G.; Xu, H., Science of Synthesis: DNA-Encoded Libraries, (2024) 1, 151.
General Introduction
Heteroatoms are important components in drug molecules because they can not only modulate bioactivity through hydrogen bonding and dipole interactions, but also adjust drug-like properties by altering the molecular absorption, distribution, metabolism, and excretion (ADME) properties. In view of this, the development of new methods for DNA-compatible carbon—heteroatom bond construction has received significant attention. This chapter summarizes the latest progress in on-DNA C—X (X = N, O, P, S, Se) bond construction methods.
M—M eeee eeeeeee eeeeeeeee (eee Meeeeee 8.8.8.8) eeeeeee eee eee eeee eeeeeeee ee eeeeee—eeeeeeeeee eeee eeeeeee eeeeeeeee eeee ee eeeeeeeeee MMM-eeeeeee eeeeeeeee (MMMe) (Meeeee 8). Meee ee eeeeeee, eeeee eee eeeeeee ee eeee-eeeeeeeeeee M—M eeee eeeeeee eeeeeeeee ee eeeeeee eee eeee eeeeeee ee eee eeeeee eee eeeeeeeee eeeeeeeeee ee eeeeeeeeeeee eeeeeeeee eeeee-eeeeeeeeee eeeeeeee eeeeee. Meeeeeeee-eeeeeeee Meeeeeee–Meeeeee eeeeeeee eee eeeeee-eeeeeeee Meeeee-eeee eeeeeeee eeeeeee MMM-eeeeeeeeee eeee (eeeeee)eeeeeee 8 eee eeeeee,[8–8] eee eeeeeeeeeeee eeeeeeee eeeeeeeeeeee (MMMe) eeeeeeee ee MMM-eeeeeeeeee eeeeee eeeeeeeee eee eeeeeeee eeeeeeeeee eeee ee eeeeeeeeeeeeeee eee 8-eeeeeeeee eeeeeeeee 8 eeee eeeeee eee eeeeee eeee eeeeeeeeee eee ee-MMM eeeeeeeee ee M(ee8)—M eeeee.[8,8] Mee eeeeeee eee ee-MMM eeeeeeeeeeee ee M(ee8)—M eeeee eeeeeee eeeeeeeeee ee MMM-eeeeeeeeee eeeeeeee eee eeeeeeeeee 8 (M = M, M),[8,88] eeeeeeeee-eeeeeeee eeeeeeeeeeeeee ee MMM-eeeeeeeeee eeeeeeeeeee 8,[88] eeeeeeeee eeeeeeeee eeeeeeeee MMM-eeeeeeeeee eeeeeee ee eeeeeeeee 8 eee eeeeee (ee eeee eeeee),[88,88] eeeeeeeeeeee eeeeeeeeeeee (MM8) eeeeeeee ee MMM-eeeeeeeeee eeeee eeeeeee 8,[88] eee eee eeeeeeeeeee eeeeeeee ee MMM-eeeeeeeeee eeeeee π-eeeeeeeee eeeeeeee 8 eeee eeeeee.[88] Meee eeee ee-MMM eeeeeeeee eeeeeeeee eee eeeeeee ee e eeeeeeee eeeeeee ee eeee eeeeee (Meeeeee 8.8).
Meeeee 8 Meeeeee eee Me-MMM M—M Meee Meeeeeeee[8–88]
Me eeeee eeeeeeee ee eee ee-MMM M—M eeee eeeeeee eeeeeeeee, eeeeeeeee eeee e eeeeeee eeeeee ee M—M eeee eeeeeeeee eeeeeee (eee Meeeeee 8.8.8.8) eeee eeee eeeeeeee, eeeeee eeeeeeeee eeeeeeeeeeee eeeeeeee eeeeeeeeeeee (MMMe) ee eeeeee eeeeeeeeeeee ee eeeeee eeeeeeeee eeeeeeee eeeeeeeeee 8,[8,88] eeeeeeeeeeee eeee eeeeeee ee eeeeeeeeee 8 ee eeeeee eeeeeeeeeeee,[8] ee eeeeeeeee eeeeeeeeeeeee ee ee-MMM eeeeeeeeeeee eeeeeeeeeee 88 (Meeeee 8).[88]
Meeeee 8 Meeeeee eee Me-MMM M—M Meee Meeeeeeee[8,8,88,88]
Meeeeee eeee eeee eeee eeeeeeeee eee ee-MMM M(ee8)—M eeee eeeeeeeee (eee Meeeeee 8.8.8.8) eeeeeee eeeeeeeeee-eeeee-eeeeeeeee eeeeee eeeeeeee ee eeee eeeeeee 88 eeee eeeeee,[88] eeeeeeeee eeeeeeee ee eeeeeeee-eeee eeeeee (MMMe) 88 eeee eeeeee,[88] eee eeeeeeeeeeee eeeeeeee eeeeeeeeeeee eeeeeeee (MMMe) ee eeeeee eeee eeeeee eeeeeeeee eeeeeeee eeeeeeeeee 88.[88] Meeeeee eee ee-MMM M(ee8)—M eeeeeeeee eeeeeee MMMM-eeeeeee eeeeeeeeeeee eeeeeeeee eeeeeeeee eeeeeee MMM-eeeeeeeeee eeeee eeeeeeee 88 eee eeeeee[88] eee eeeeeeeeeee eeeeeeee ee eeeeee π-eeeeeeeee eeeeeeee 88 eeee eeeeee (Meeeee 8).[88] Me eeeeeeeeee, eee eeeeeeeeee eeeeeeeeee ee eeeee eeeeeee (MMMM) eeeeeeee eee eeeeeeee e eeeeee eeeeee eeee ee eeeeeeeee eeeeeeeeeeee M—M eeeeeeeee ee ee-MMM eeeeeeeee. Meeeeeee eeeeeee eeeeee-eeeeeeee eeeee eeeeeeee ee MMM-eeeeeeeeee eeee eeeeeee 88 eeee eeeeee, eeeeeeeee eeeeeeeee eee eeeeeeeeeeee eeeeeeeeeeee ee eeeeee eeee MMM-eeeeeeeeee eeeee eeeeeeee 88 (eee eeeeeeeeee eeeeeeeee ee eeeeeeeeee), M—MM8M8 eeeeeee eeee eeeeeeeee eee eeeeeeeeeeee eeeeeeeeeeee eeee eeeeeeeeee ee MMM-eeeeeeeeee eeeee eeeeeeee 88, eee eeeeeee eeeeeee eeeeeeeee eeeee MMM-eeeeeeeeee eeeeeeee-eeee eeee eeeeeee 88 eee eeeeeeeeee.[88,88]
Meeeee 8 Meeeeee eee Me-MMM M—M Meee Meeeeeeee[88,88,88–88]
Meeeeee eee ee-MMM M—Me eeee eeeeeeeee (eee Meeeeee 8.8.8.8) eeee eeee eeee eeeeeeee eeeeeee eeeeee eeeeeeeee eeeeeeeeeeee eee MMMM-eeeeeee eeeee-eeeeeeee eeeeeee eeeeeeeeeeee ee eeeeeeee-eeee eeeeee 88 eeee e eeeeeeee eeeeeeee eeeeee (e.e., M88Me8, M8MeMe, M8MeM),[88,88] eee eeee(eeeeeeeeeeeeeee)eeeeee- ee eeeeeee(MMM)-eeeeeeee M—M eeeeeeeeeeeeeeee ee MMM-eeeeeeeeee eeeeeee eeee eeeeeeeeeeeeee-8-eeee (Meeeee 8).[88,88]
Meeeee 8 Meeeeee eee Me-MMM M—Me Meee Meeeeeeee[88–88]
Me eee, eeeeeee eee ee-MMM M—M eeee eeeeeeeee (eee Meeeeee 8.8.8.8) eee eee eeee eeeeeeeee, eee eeee e eee eeeeeee eeee eeeeeee eeeeeeee eeee eeee eeeeeeee (Meeeee 8). Meeee eeeeeee eeeeeeeee-eeeeeeee eeeeeeeeeeeeeee ee MMM-eeeeeeeeee eeee eeeeeeeeeeeeeeee 88 eeee eeee M-eeeeeeeeeeee,[88] MMMM-eeeeeee, eeeeee-eeeeeeee M—M eeeee eeeeeeee eeeeeee MMM-eeeeeeeeee eeee eeeeeee 88 eee eeeeeeeeeeeeeeee,[88] eee eee eeeee-eeeeeeeeeeeeeee eeeeeeee (MMM) eeeeeeee eeeeeee MMM-eeeeeeeeee eeeeeeeeeeeeeeeeeeeeeee 88 eee eeeeeeeeee.[88]
Meeeee 8 Meeeeee eee Me-MMM M—M Meee Meeeeeeee[88,88,88]
References
[1] | Me, M.; Meeeeee, M. M.; Meeeeeee, M. M.; Meeee, M. M., Mee. Meee. Meeeee., (8888) 8, 8888. |
[2] | ee Meeee Meeee, M.; Meeeee, M.; Meeeeee-Meeeíeee, M.; Meeeáeee, M.; Meeeeeeee, M.; Meee, M.; Meeeíe-Meeeee, M. M.; Meeeee, M. M.; Meeeeeee, M.; Meeeeee, M., MMM Meee. Mee., (8888) 88, 88. |
[3] | Me, M.; Me, M.; Meee, M.; Mee, M.; Meeee, M.; Me, M.; Me, M.; Meee, M.; Me, M.; Meee, M.; Meeeee, M. M., Mee. Mee. (Meeeeeee, Mee.), (8888) 8, 8888 888. |
[4] | Meee, M.-M.; Meeee, M. M.; Me, M. M.; Meeeeeee, M.; Meeeee, M.; Meeeee, M. M.; Meeeee, M. M.; Meeeee, M. M.; Me, M.; Meeeeee, M., Meeeeeeeeeee Meee., (8888) 88, 888. |
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[6] | Meee, M.; Meeee, M., Mee. Meee. Meeeee., (8888) 8, 8888. |
[7] | Meee, M.; Meee, M.; Meeeeeeee, M. M.; Meeee, M.; MeMeeee, M. M.; Meeee, M. M., MMM Meee. Mee., (8888) 88, 888. |
[8] | Me, M.; Meeeeeee, M. M.; Meee, M.; Meeeeeee, M.; Meeee, M.; Meeeee, M. M.; Meeeeeee, M. M.; Meee, M.; Meeee, M. M.; Mee, M.; Meeeeeeee, M.; Meeeeeee, M.; Meeeeeee, M. M.; Meeeeeee, M.; Meeeee, M. M.; Meee, M.; Meee, M.; Meeeeeeeeee, M.; Meeeeeeee, M. M.; Meeeee, M. M.; Meee, M. M.; Meeeee, M. M., MMM Meee. Mee., (8888) 88, 888. |
[9] | Meee, M.; Mee, M.; Mee, M.; Mee, M.; Mee, M.; Mee, M.; Me, M.; Mee, M.; Meee, M.; Meeee, M.; Meee, M.; Meeee, M.; Mee, M.; Me, M., Meee. Mee., (8888) 88, 8888. |
[10] | Mee, M.; Meeee, M. M., MeeeMeeMeee, (8888) 88, 888. |
[11] | Mee, M.; Mee, M.; Mee, M.; Mee, M.; Me, M.; Mee, M.; Mee, M., Meeee. Meee., (8888) 88, 888888. |
[12] | Meeeeeee, M. M.; Meeeee, M.; Mee Meeeeeee, M.; Meeeeee, M.; Meeee, M.; Meeeeeeeee, M.; Meeeeeeeeee, M.; Meee, M.; Meee, M., Meeeeeeeeeee Meee., (8888) 88, 8888. |
[13] | Meeee, M. M.; Meee, M.; Meeee, M.; Meee, M.; Meee, M.; Meeee, M. M.; Meeeeeeeee, M. M.; Meeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeeee, M.; Meeee, M. M.; Meeeee, M. M.; Meee, M. M.; Meeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[14] | Meeee, M.; Meee, M.; Meee, M.; Meeee, M.; Me, M.; Me, M., Mee. Meee., (8888) 88, 8888. |
[15] | Meee, M.-M.; Mee, M.; Meeee, M.-M.; Meee, M.-M.; Meee, M.-M.; Meee, M.; Meee, M.; Meee, M.; Meeeeeee, M.; Me, M.-M.; Meeee, M., eMeeeeee, (8888) 88, 888. |
[16] | Meeeee, M.; Me, M.; Meeeeeeeee, M. M.; Meeee, M.; Meee, M.; Meeee Meeeeeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meeeeee, M. M., MeeeMeeMeee, (8888) 88, 888. |
[17] | Meeee, M. M.; Meeee, M.; Me, M.; Meee, M.; Meee, M.; Meeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeeee, M.; Meeeeeee, M. M.; Meeeeeeeee, M. M.; Möeeee, M. M.; Mee, M.; Meee, M.-M.; Meee, M. M.; Meeee, M. M.; Meeeee, M. M., Meeee. Meee. Mee. Me., (8888) 88, 8888. |
[18] | Meee, M.; Meee, M.; Mee, M.; Mee, M.; Meeee, M.; Mee, M.; Me, M.; Me, M., Meee. Mee., (8888) 88, 8888. |
[19] | Mee, M.; Me, M.; Meee, M.; Meeee, M.; Meee, M.; Me, M.; Mee, M.; Meeee, M., Mee. Meee., (8888) 88, 8888. |
[20] | Me, M.; Meee, M.; Meee, M.; Meeee, M.; Me, M.; Meeee, M.; Meee, M.; Me, M.; Mee, M. M.; Me, M.; Mee, M.; Me, M.; Me, M.; Meee, M.; Mee, M., Meeee. Meee. Mee. Me., (8888) 88, e888 888 888. |
[21] | Me, M.; Me, M.; Meeee, M.; Meeee, M.; Me, M.; Me, M.; Me, M.; Mee, M.; Me, M.; Mee, M.; Meee, M.; Meeeee, M. M., Meeee. Meee. Mee. Me., (8888) 88, 88888. |
[22] | Meeee, M.; Meee, M.; Mee, M.; Me, M.; Meeee, M.; Me, M.; Meee, M.; Mee, M.; Meee, M.; Me, M.; Me, M., Meee. Meeeee. (Meeeeeeee), (8888) 88, 8888. |
[23] | Mee, M.; Meee, M.; Mee, M.; Me, M.; Me, M., Mee. Meee., (8888) 88, 8888. |