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Chemical Structure| 55750-62-4 Chemical Structure| 55750-62-4
Chemical Structure| 55750-62-4

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BMPS is a nonclaevable ADC linker used in the synthesis of antibody-drug conjugates (ADCs).

Synonyms: BMPS

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Product Details of 3-(Maleimido)propionic acid N-hydroxysuccinimide ester

CAS No. :55750-62-4
Formula : C11H10N2O6
M.W : 266.21
SMILES Code : C(C(ON1C(CCC1=O)=O)=O)CN2C(C=CC2=O)=O
Synonyms :
BMPS
MDL No. :MFCD00043141
InChI Key :JKHVDAUOODACDU-UHFFFAOYSA-N
Pubchem ID :4620597

Safety of 3-(Maleimido)propionic acid N-hydroxysuccinimide ester

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 3-(Maleimido)propionic acid N-hydroxysuccinimide ester

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 55750-62-4 ]

[ 55750-62-4 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 55750-62-4 ]
  • [ 1615234-93-9 ]
  • [ 1263045-16-4 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; Referring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-blc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
0.227g With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; [0277] Referring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-boc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
  • 2
  • [ 55750-62-4 ]
  • [ 756525-91-4 ]
  • [ 1263045-16-4 ]
YieldReaction ConditionsOperation in experiment
0.227 g Synthesis of linker-drugReferring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-boc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
  • 3
  • [ 55750-62-4 ]
  • [ 474645-27-7 ]
  • C46H72N6O10 [ No CAS ]
  • 4
  • [ 55750-62-4 ]
  • [ 29390-67-8 ]
  • 6-deoxy-6-(3'-(N-maleimido)-propionamido)-β-cyclodextrin [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In water; N,N-dimethyl-formamide; at 20℃; for 3h; 6-Amino-6-deoxy-P-cyclodextrin (1) was synthesized according to a literature method (Weihua, T., Siu-Choon, N., Nature Protocol, 2008, 3: 691-695). Compound 1 (115 mg, 0.10 mmol) was dissolved in deionised water (6 mL) and 3-(N-maleimido)-propionic acid N-hydroxysuccinimide ester (54 mg, 0.20 mg) was added in DMF (1.4 mL). The mixture was stirred for 3 h at room temperature, then the product (2) was precipitated with acetone and washed several times with acetone (yield 101 mg, 79%). HI -NMR (400 MHz, DMSO-d6): delta 6.97 (s, 2H), 5.73 (m, 14H), 4.82 (s, 7H), 4.67 (m, 7H), 3.82-3.47 (m, 30 H).; 13C-NMR (101 MHz, DMSO-d6): delta 171.1, 134.9, 102.4, 82.0, 73.5, 72.9, 72.5, 60.4.; ESI-MS (m/z): 1307.66 [M + Na]+.; Molecular weight: 1285.11894; molecular formula: C49H76N2O37
  • 5
  • [ 663921-15-1 ]
  • [ 55750-62-4 ]
  • [ 1263045-16-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; at 20℃; for 2h; Compound 3-11 (4.55 g, 18.7 mmol) was dissolved in 10 mL water, NaHCO3 (1.71 g, 20.4 mmol) was added and the mixture was stirred. CE-L-055 (4.55 g, 17 mmol) in 30 mL 1,2-dimethoxyethane was added dropwise slowly. The reaction mixture was stirred for 2 hours at room temperature. 50 mL water was added, the mixture was adjusted to pH 3-4 with 1 M dilute hydrochloric acid, and then extracted with EtOAc for 10 times (50 mL×10). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to give the crude product, which was used directly for the next step. LCMS (ESI) m/z 417.2 (M+H)+.
 

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