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Merck
CN

943592

(S,R,S)-AHPC-C4-NH2 hydrochloride

≥95%

Synonym(s):

(2S,4R)-1-[(S)-2-(5-Aminopentanamido)-3,3-dimethylbutanoyl]-4-hydroxy-N-[4-(4-methylthiazol-5-yl)benzyl]pyrrolidine-2-carboxamide, N-(5-amino-1-oxopentyl)-3-methyl-L-valyl-4-hydroxy-N-[[4-(4-methyl-5-thiazolyl)phenyl]methyl]-, L-Prolinamide

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SMILES string

O=C(NC(C(=O)N1CC(O)CC1C(=O)NCC=2C=CC(=CC2)C=3SC=NC3C)C(C)(C)C)CCCCN

InChI key

BJFSHNWASBGXMS-ZFGGDYGUSA-N

InChI

1S/C27H39N5O4S/c1-17-23(37-16-30-17)19-10-8-18(9-11-19)14-29-25(35)21-13-20(33)15-32(21)26(36)24(27(2,3)4)31-22(34)7-5-6-12-28/h8-11,16,20-21,24,33H,5-7,12-15,28H2,1-4H3,(H,29,35)(H,31,34)/t20-,21+,24-/m1/s1

assay

≥95%

form

solid

storage condition

protect from light

color

light yellow to green

functional group

amine

storage temp.

−20°C

Quality Level

100

General description

This compound is a synthetic E3 ligase ligand–linker conjugate that integrates the (S,R,S)-AHPC VHL-binding motif with a four-carbon alkyl linker terminating in a primary amine—facilitating conjugation to target ligands. It was developed for constructing EED-targeted PROTACs, effectively directing cereblon-like VHL-mediated ubiquitination pathways

Application

  • PROTAC construction, especially for creating EED-targeting bifunctional degraders.
  • Chemical biology studies utilizing VHL-mediated degradation.
  • Medicinal chemistry, where modular, functionalized E3 ligase ligands are needed.
  • Amine functional group is ideal for coupling reactions—e.g., amide bond formation with carboxylic acids or NHS esters.
  • Linker flexibility ensures manageable conjugation without compromising binding moiety orientation.
  • Peptidic core maintains chirality; reactions should avoid racemizing conditions.

Features and Benefits

  • PROTAC-ready VHL ligand with tethered linker for modular assembly.
  • Hydrophilic handle (aminopentyl tail) supports efficient conjugation and solubility.
  • Amine functional group is ideal for coupling reactions—e.g., amide bond formation with carboxylic acids or NHS esters.
  • Linker flexibility ensures manageable conjugation without compromising binding moiety orientation.
  • Peptidic core maintains chirality; reactions should avoid racemizing conditions.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000518487
0000518487

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