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905380

Sigma-Aldrich

(S,R,S)-AHPC-C6-PEG3-butyl chloride

≥95%

Synonym(s):

(2S,4R)-1-((S)-2-(tert-Butyl)-22-chloro-4-oxo-10,13,16-trioxa-3-azadocosanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide, (S,R,S)-AHPC-6-2-2-6-Cl, Crosslinker−E3 Ligase ligand conjugate, Protein degrader building block for PROTAC® research, Template for synthesis of targeted protein degrader, VH032 conjugate

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About This Item

Empirical Formula (Hill Notation):
C38H59ClN4O7S
CAS Number:
1835705-55-9
Molecular Weight:
751.42
MDL number:
MFCD31560478
UNSPSC Code:
12352101
NACRES:
NA.22

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ligand

VH032

assay

≥95%

form

solid

reaction suitability

reactivity: sulfuryl reactive
reagent type: ligand-linker conjugate

functional group

alkyl halide

storage temp.

2-8°C

SMILES string

ClCCCCCCOCCOCCOCCCCCC(N[C@H](C(N1[C@H](C(NCC2=CC=C(C3=C(C)N=CS3)C=C2)=O)C[C@@H](O)C1)=O)C(C)(C)C)=O

InChI

1S/C38H59ClN4O7S/c1-28-34(51-27-41-28)30-15-13-29(14-16-30)25-40-36(46)32-24-31(44)26-43(32)37(47)35(38(2,3)4)42-33(45)12-8-7-11-19-49-21-23-50-22-20-48-18-10-6-5-9-17-39/h13-16,27,31-32,35,44H,5-12,17-26H2,1-4H3,(H,40,46)(H,42,45)/t31-,32+,35-/m1/s1

InChI key

MLRLOIWXHCPWFF-MEEYNGGZSA-N

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This Item
905399905232904864
(S,R,S)-AHPC-C6-PEG3-butyl chloride ≥95%

Sigma-Aldrich

905380

(S,R,S)-AHPC-C6-PEG3-butyl chloride

(S,R,S)-AHPC-PEG2-butyl chloride

Sigma-Aldrich

905399

(S,R,S)-AHPC-PEG2-butyl chloride

(S,R,S)-AHPC-C6-PEG3-butyl amine hydrochloride ≥95%

Sigma-Aldrich

905232

(S,R,S)-AHPC-C6-PEG3-butyl amine hydrochloride

(S,R,S)-AHPC-PEG6-butyl azide ≥95%

Sigma-Aldrich

904864

(S,R,S)-AHPC-PEG6-butyl azide

reaction suitability

reactivity: sulfuryl reactive, reagent type: ligand-linker conjugate

reaction suitability

reactivity: sulfuryl reactive, reagent type: ligand-linker conjugate

reaction suitability

reactivity: carboxyl reactive, reagent type: ligand-linker conjugate

reaction suitability

-

assay

≥95%

assay

≥95%

assay

≥95%

assay

≥95%

functional group

alkyl halide

functional group

alkyl halide

functional group

amine

functional group

azide

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

form

solid

form

liquid

form

powder or crystals

form

liquid

ligand

VH032

ligand

VH032

ligand

VH032

ligand

VH032

Application

Protein degrader builiding block (S,R,S)-AHPC-C6-PEG3-butyl Chloride enables the synthesis of molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This conjugate contains a von Hippel–Lindau (VHL)-recruiting ligand, a linker with both hydrophobic and hydrophilic moieties, and a pendant chloroalkane for reactivity with a nucleophilic group on a target ligand. Because even slight alterations in ligands and crosslinkers can affect ternary complex formation between the target, E3 ligase, and PROTAC, many analogs are prepared to screen for optimal target degradation. When used with other protein degrader building blocks with a pendant chloro group, parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Other Notes

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC® Degraders for Targeted Protein Degradation

Modular PROTAC Design for the Degradation of Oncogenic BCR-ABL

Targeted Protein Degradation by Small Molecules

Small-Molecule PROTACS: New Approaches to Protein Degradation

Targeted Protein Degradation: from Chemical Biology to Drug Discovery

Impact of linker length on the activity of PROTACs

Legal Information

PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license

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Description
Pricing

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(S,S,S)-AHPC hydrochloride, ≥97%

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Pomalidomide-C6-CO2H, ≥98%

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Pomalidomide-C3-CO2H, ≥95%

901503

(S,R,S)-AHPC-PEG1-Alkyne, ≥95%

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(S,R,S)-AHPC-PEG3-NH2 hydrochloride, ≥95%

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Pomalidomide-PEG3-CO2H, ≥95%

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(S,R,S)-AHPC-PEG2-Alkyne, ≥95%

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Pomalidomide-PEG1-NH2 hydrochloride, ≥95%

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(S,R,S)-AHPC-PEG3-Alkyne, ≥95%

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(S,R,S)-AHPC-C6-CO2H hydrochloride

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Pomalidomide-PEG2-Alkyne, ≥95%

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t-Boc-N-amido-PEG3-CH2CO2H, ≥95%

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Bromo-PEG2-acid, ≥95%

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Bromo-PEG3-acid

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Propargyl-PEG1-acid, ≥95%

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Propargyl-PEG2-acid

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Bromo-PEG1-acid, ≥95%

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Propargyl-PEG3-acid

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Pomalidomide-PEG6-Alkyne

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Pomalidomide-PEG5-Alkyne, ≥95%

901833

Pomalidomide-PEG4-Alkyne

901832

Pomalidomide-PEG6-NH2 hydrochloride, ≥98%

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Pomalidomide-PEG5-NH2 hydrochloride

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Pomalidomide-PEG4-NH2 hydrochloride, ≥95%

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Pomalidomide-PEG6-CO2H

901828

Pomalidomide-PEG5-CO2H, ≥95%

901824

Pomalidomide-PEG4-CO2H

901860

(S,R,S)-AHPC-PEG6-NH2 hydrochloride, ≥95%

901855

(S,R,S)-AHPC-PEG5-Alkyne

901851

(S,R,S)-AHPC-PEG4-Alkyne

901850

(S,R,S)-AHPC-PEG5-NH2 hydrochloride

901848

(S,R,S)-AHPC-PEG4-NH2 hydrochloride, ≥95%

901873

(S,R,S)-AHPC-PEG6-Alkyne

902691

Hydroxy-PEG5-t-butyl ester

902683

BocNH-PEG5-acid

902667

Propargyl-PEG6-acid

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Propargyl-PEG4-acid

902586

Hydroxy-PEG4-t-butyl ester

902578

Hydroxy-PEG6-t-butyl ester, ≥95%

903434

Pomalidomide-PEG6-butyl azide, ≥95%

903442

Pomalidomide-PEG6-butyl iodide, ≥95%

903833

Pomalidomide-PEG2-azide

903825

Pomalidomide-PEG1-azide

903957

(S,R,S)-AHPC-PEG1-azide

904651

(S,R,S)-AHPC-PEG3-azide, ≥95%

904724

Pomalidomide-PEG2-butyl iodide, ≥95%

904708

Pomalidomide-C6-PEG3-butyl iodide, ≥95%

904678

Pomalidomide-PEG3-azide

904686

Pomalidomide-C6-PEG3-butyl azide, ≥95%

904813

(S,R,S)-AHPC-PEG2-azide

904821

(S,R,S)-AHPC-C6-PEG3-butyl azide, ≥95%

904880

Pomalidomide-C6-PEG1-C3-PEG1-butyl azide, ≥95%

904872

Pomalidomide-PEG2-butyl azide, ≥95%

904864

(S,R,S)-AHPC-PEG6-butyl azide, ≥95%

905178

(S,R,S)-AHPC-C6-PEG1-C3-PEG1-butyl azide, ≥95%

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(S,R,S)-AHPC-PEG2-butyl azide, ≥95%

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(S,R,S)-AHPC-C6-PEG3-butyl amine hydrochloride, ≥95%

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Pomalidomide-C6-PEG3-butyl amine hydrochloride, ≥98%

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(S,R,S)-AHPC-PEG2-butyl chloride

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(S,R,S)-AHPC-C6-PEG3-butyl chloride, ≥95%

905402

(S,R,S)-AHPC-C6-PEG1-C3-PEG1-butyl chloride, 95%

906050

Pomalidomide-C6-PEG1-C3-PEG1-butyl iodide, ≥95%

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(S,R,S)-AHPC-PEG2-butyl amine hydrochloride

907677

(S,R,S)-AHPC-PEG6-butyl chloride

909378

(S,R,S)-AHPC-PEG6-Azide, ≥95%

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Pomalidomide-PEG4-Azide, ≥95%

909394

Pomalidomide-PEG5-azide, ≥95%

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Pomalidomide-PEG6-azide, ≥95%

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(S,R,S)-AHPC-PEG4-Azide, ≥95%

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6-(2-(2-(Oct-7-yn-1-yloxy)ethoxy)ethoxy)hexanoic acid, ≥90%

910449

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910600

(S,R,S)-AHPC-PEG2-butyl CO2H, ≥95%

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(S,R,S)-AHPC-PEG6-butyl alkyne, ≥95%

910554

(S,R,S)-AHPC-PEG6-butyl CO2H, ≥95%

910546

(S,R,S)-AHPC-C6-PEG3-butyl alkyne, ≥95%

910538

(S,R,S)-AHPC-PEG2-butyl alkyne, ≥95%

910511

Pomalidomide-C6-PEG3-butyl alkyne, ≥95.0%

910503

Pomalidomide-PEG2-butyl alkyne, ≥95%

910481

Pomalidomide-PEG6-butyl CO2H, ≥95%

911003

Pomalidomide-PEG2-butyl amine hydrochloride, ≥95%

911801

AHPC-C6-PEG1-C3-PEG1-butyl amine hydrochloride, ≥90%

911690

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911666

Pomalidomide-C6-NH2 hydrochloride, ≥95%

911658

Pomalidomide-C3-NH2 hydrochloride, ≥95%

911763

C5 Lenalidomide-PEG1-piperazine hydrochloride, ≥95%

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Pomalidomide-C6-PEG1-C3-PEG1-butyl amine hydrochloride, ≥95%

915572

Pomalidomide-dipiperazine-NH2 hydrochloride, ≥95%

916536

Pomalidomide-piperazine-pyridine-alkyne-NH2 hydrochloride

917729

C5 Lenalidomide-piperazine-pyridine-alkyne-NH2 hydrochloride, ≥95%

917303

C5 Lenalidomide-C6-PEG1-C3-PEG1-Butyl NH2 hydrochloride, ≥95%

917818

(S,R,S)-AHPC-C9-NH2 hydrochloride, ≥95%

919357

(S,R,S)-AHPC-PEG1-piperazine hydrochloride, ≥95%

919489

CCW16-C6-PEG3-butyl-BocNH

918687

(S,R,S)-AHPC-alkyne-piperidine hydrochloride

919969

C5 Lenalidomide-PEG2-Butyl NH2 hydrochloride, ≥95%

919896

C5 Lenalidomide-dipiperazine-NH2 hydrochloride

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCJ6872

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Ashton C Lai et al.
Angewandte Chemie (International ed. in English), 55(2), 807-810 (2015-11-26)
Proteolysis Targeting Chimera (PROTAC) technology is a rapidly emerging alternative therapeutic strategy with the potential to address many of the challenges currently faced in modern drug development programs. PROTAC technology employs small molecules that recruit target proteins for ubiquitination and
Momar Toure et al.
Angewandte Chemie (International ed. in English), 55(6), 1966-1973 (2016-01-13)
The current inhibitor-based approach to therapeutics has inherent limitations owing to its occupancy-based model: 1) there is a need to maintain high systemic exposure to ensure sufficient in vivo inhibition, 2) high in vivo concentrations bring potential for off-target side effects, and 3) there is
Kedra Cyrus et al.
Molecular bioSystems, 7(2), 359-364 (2010-10-06)
Conventional genetic approaches have provided a powerful tool in the study of proteins. However, these techniques often preclude selective manipulation of temporal and spatial protein functions, which is crucial for the investigation of dynamic cellular processes. To overcome these limitations
Philipp M Cromm et al.
Cell chemical biology, 24(9), 1181-1190 (2017-06-27)
Traditional pharmaceutical drug discovery is almost exclusively focused on directly controlling protein activity to cure diseases. Modulators of protein activity, especially inhibitors, are developed and applied at high concentration to achieve maximal effects. Thereby, reduced bioavailability and off-target effects can
Momar Toure et al.
Angewandte Chemie (International ed. in English), 55(6), 1966-1973 (2016-01-13)
The current inhibitor-based approach to therapeutics has inherent limitations owing to its occupancy-based model: 1) there is a need to maintain high systemic exposure to ensure sufficient in vivo inhibition, 2) high in vivo concentrations bring potential for off-target side effects, and 3) there is

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Degrader Building Blocks for Targeted Protein Degradation

Protein Degrader Building Blocks are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

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