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187223-15-0

187223-15-0 Structure

187223-15-0 Structure
IdentificationBack Directory
[Name]

FMOC-L-HYP(BOM)-OH
[CAS]

187223-15-0
[Synonyms]

Fmoc-Hyp(Bcc)-OH
Fmoc-Hyp(Bom)-OH
FMOC-L-HYP(BOM)-OH
(9H-Fluoren-9-yl)MethOxy]Carbonyl Hyp(Bom)-OH
(4R)-1-Fmoc-4-[[[(2-Boc-amino-ethyl)amino]carbonyl]oxy]-L-proline
N-alpha-(9-fluorenylmethyloxycarbonyl)-L-Hyp(Boc-aminoethylcarbamoyl)
N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-O-(TERT-BUTYLOXYCARBONYLAMINOETHYLCARBAMOYL)-TRANS-L-HYDROXYPROLINE
(2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(((2-((tert-butoxycarbonyl)amino)ethyl)carbamoyl)oxy)pyrrolidine-2-carboxylic acid
(2S,4R)-4-{[(2-{[(tert-butoxy)carbonyl]amino}ethyl)carbamoyl]oxy}-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}pyrrolidine-2-carboxylic acid
(2S,4R)-4-[[[[2-[[(1,1-Dimethylethoxy)carbonyl]amino]ethyl]amino]carbonyl]oxy]-1,2-pyrrolidinedicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester
1,2-Pyrrolidinedicarboxylic acid, 4-[[[[2-[[(1,1-diMethylethoxy)carbonyl]aMino]ethyl]aMino]carbonyl]oxy]-, 1-(9H-fluoren-9-ylMethyl) ester, (2S,4R)-
[EINECS(EC#)]

630-406-9
[Molecular Formula]

C28H33N3O8
[MDL Number]

MFCD07366898
[MOL File]

187223-15-0.mol
[Molecular Weight]

539.58
Chemical PropertiesBack Directory
[Boiling point ]

749.0±60.0 °C(Predicted)
[density ]

1.35±0.1 g/cm3(Predicted)
[storage temp. ]

2-8°C
[form ]

Solid
[pka]

3.55±0.40(Predicted)
[color ]

White to pink
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H317
[Precautionary statements ]

P261-P272-P280-P302+P352-P333+P313-P321-P363-P501
Hazard InformationBack Directory
[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]

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)-

187223-14-9

FMOC-L-HYP(BOM)-OH

187223-15-0

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%.

[IC 50]

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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