| Identification | Back Directory | [Name]
D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1:1), (4R)- | [CAS]
114676-59-4 | [Synonyms]
Cis-D-Hyp-OMe.HC
Cis-D-Hyp-OMe.HCl
D-Proline, 4-Hydroxy
Cis-4-Hydroxy-D-proline Methyl ester HCl
Methyl cis-4-Hydroxy-D-proline Hydrochloride
Methyl 4-hydroxypyrrolidine-2-carboxylate HCl
D-Proline, 4-hydroxy-, methyl ester (hydrochloride)
Cis-4-hydroxy-proline Methyl ester hydrochloride -D-
D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1
D-Proline, 4-hydroxy-, Methyl ester, hydrochloride, (4R)-
(2R,4R)-cis-4-hydroxy-D-proline methyl ester hydrochloride
D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1:1), (4R)-
Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride
D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1:1), (4...
(2R,4R)-4-Hydroxypyrrolidine-2-carboxylic acid methyl ester hydrochloride
(2R,4R)-4-Hydroxy-2-(methoxycarbonyl)pyrrolidine hydrochloride, cis-4-Hydroxy-D-proline methyl ester hydrochloride | [Molecular Formula]
C6H11NO3.ClH | [MDL Number]
MFCD00082536 | [MOL File]
114676-59-4.mol | [Molecular Weight]
181.618 |
| Chemical Properties | Back Directory | [Melting point ]
121-123℃ | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
solid | [color ]
White | [Optical Rotation]
10.30(C=1.00g/100ml MEOH) |
| Hazard Information | Back Directory | [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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