LC-SMPH

 CAS No.: 1357178-31-4  Cat No.: BP-502150  Purity: ≥ 98% 4.5  

LC-SMPH is a bifunctional PROTAC linker reagent designed to connect a target-binding ligand to an E3 ligase recruiter through a stable, linker-mediated geometry that supports formation of a productive ternary complex. Structurally, it contains an NHS ester for reaction with primary amines and a maleimide for selective reaction with thiols, connected by a long-chain amide-containing spacer that preserves conformational freedom between the two conjugation sites. In PROTAC architectures, such linkers are critical determinants of degradation efficiency because they tune the effective distance and relative orientation between the warhead and the recruited E3 ligase, thereby influencing ubiquitin transfer and subsequent proteasomal processing. LC-SMPH is therefore valuable for researchers optimizing targeted protein degradation constructs, particularly when iterative linker length and attachment-site compatibility are required to maximize potency and selectivity in cellular degradation assays.

LC-SMPH

Structure of 1357178-31-4

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Category
PROTAC Linker
Molecular Formula
C23H32N4O8
Molecular Weight
492.52
Appearance
White powder

* For research and manufacturing use only. Not for human or clinical use.

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Purity
≥ 98%
Appearance
White powder
Storage
Store at -20 °C
IUPACName
(2,5-dioxopyrrolidin-1-yl) 6-[6-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]hexanoylamino]hexanoate
Synonyms
N-(3-(4-(methylthio)phenyl)thiazol-2-yl)-N'-(4-methylphenyl)urea; Succinimidyl-4-[N-maleimidomethyl]cyclohexane-1-carboxy-[6-amidocaproate]
InChI Key
BIKSMXURUVXRPH-UHFFFAOYSA-N
InChI
InChI=1S/C23H32N4O8/c28-17(24-14-6-2-4-8-23(34)35-27-21(32)11-12-22(27)33)7-3-1-5-15-25-18(29)13-16-26-19(30)9-10-20(26)31/h9-10H,1-8,11-16H2,(H,24,28)(H,25,29)
SMILES
C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCCCCNC(=O)CCN2C(=O)C=CC2=O

LC-SMPH is a PROTAC linker designed to support efficient conjugation between a target-binding ligand and an E3 ligase-recruiting moiety, enabling proximity-driven ubiquitination and degradation. Its structure is tailored to provide a stable, chemically addressable connection point while maintaining compatibility with common bioconjugation workflows used in targeted protein degradation research. The details below describe its structural features and practical considerations for assembling PROTACs using this linker.

Structure: LC-SMPH is a linker bearing a sulfonamide-type connection motif, providing a polar, hydrogen-bonding capable framework. It contains heteroatom-rich functional groups that can influence solubility and conformational behavior. The covalent backbone supports robust amide/sulfonamide chemistry for stable conjugate formation.

Reactivity: LC-SMPH is suitable for linker incorporation via standard coupling strategies used in PROTAC synthesis, typically involving amide or sulfonamide-forming transformations. Reactions are commonly performed under dehydrating or activating conditions to promote nucleophilic substitution at the activated electrophile. Base and inert atmosphere are frequently used to suppress side reactions, with polar aprotic solvents often improving coupling efficiency. Purification is typically achieved by chromatography to remove unreacted starting materials and byproducts.

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L

* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
g/mol
g

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