D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1:1), (4R)- Chemical Properties

Melting point:

121-123℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

color 

White

optical activity

10.30(C=1.00g/100ml MEOH)

Safety Information

HS Code 

2933998090

D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1:1), (4R)- Usage And Synthesis

Uses

D-Proline, 4-hydroxy-, methyl ester hydrochloride is a non-cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs). D-Proline, 4-hydroxy-, methyl ester hydrochloride is also a alkyl chain-based PROTAC linker that can be used in the synthesis of PROTACs[2

Synthesis

To a stirred solution of cis-4-hydroxy-D-proline (10.0 g, 76.3 mmol, 1 eq.) in methanol (300 mL) was slowly added thionyl chloride (10.0 mL, excess) over 1.5 min at 0 °C. The reaction mixture was gradually warmed to 23 °C and stirred continuously for 16 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure to afford (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid methyl ester hydrochloride as a white solid (15.9 g, 100% yield).

IC 50

Non-cleavable Linker

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

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