Uses
Fmoc-Hyp(Bom)-OH is a non-cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs). Fmoc-Hyp(Bom)-OH is also a alkyl chain-based PROTAC linker that can be used in the synthesis of PROTACs<
Synthesis
Step III: Preparation of Fmoc-(2S,4R)-(4-O-CO-NH-CH2-CH2-NH-Boc)-Pro-OH. the methyl ester obtained in step II was converted to free acid by hydrolysis reaction. This is done by adding 1N sodium hydroxide solution to a mixed solvent of 1,4-dioxane and water for the reaction. This step produced a mixture of H-(2S,4R)-(4-O-CO-NH-CH2-CH2-NH-Boc)-Pro-OH with the target product Fmoc-(2S,4R)-(4-O-CO-NH-CH2-CH2-NH-Boc)-Pro-OH. The reaction yield was 55%.
References
[1] Beck A, et al. Strategies and challenges for the next generation of antibody-drug conjugates. Nat Rev Drug Discov. 2017;16(5):315-337. DOI:
10.1038/nrd.2016.268[2] Nalawansha DA, et al. PROTACs: An Emerging Therapeutic Modality in Precision Medicine. Cell Chem Biol. 2020;27(8):998-985. DOI:
10.7554/eLife.57277
![1,2-Pyrrolidinedicarboxylic acid, 4-[[[[2-[[(1,1-diMethylethoxy)carbonyl]aMino]ethyl]aMino]carbonyl]oxy]-, 1-(9H-fluoren-9-ylMethyl) 2-Methyl ester, (2S,4R)-](/CAS/20150408/GIF/187223-14-9.gif)
