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. 2020 May 8;9(5):1169. doi: 10.3390/cells9051169

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© 2020 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

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Synthesis of the Biotin_3xNHSX-Linker: (I.) t-butylacrylate, sodium, THF, 16h, 13%, (II.) 1. NaN₃, DMF, 70 °C, 2d, 2. PPh₃, H₂O, THF, 4d, quant., (III.) t-butylacrylate, NaOH, DMSO, 15 °C and then warm up to rt, 20h, 23%, (IV.) benzyl chloroformate, Na₂CO₃ (aq.), DCM, 4d, 94%, (V.) 1. TFA, DCM, 2h, 2. (2), DIPEA, PyBoP, DMF, 24 h, 69%, (VI.) H₂, Pd/C, MeOH, 3d, 88%, (VII.) D(+)Biotin, DIPEA, PyBoP, DMF, 18h, 38%, (VII.) 1. TFA, DCM, Toluol, 2h, 2. N-hydroxysuccinimide, DCC, THF, 3d, quant. See SI and Figures S1 and S2 for details.