4-(N-Boc-amino)-1,6-heptanedioic acid - CAS 848242-88-6

Inquiry

4-(N-Boc-amino)-1,6-heptanedioic acid is a PROTAC linker, which is composed of alkyl chains. 4-(N-Boc-amino)-1,6-heptanedioic acid can be used to synthesize a range of PROTACs.

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Molecular Formula

C₁₂H₂₁NO₆

Molecular Weight

275.30

4-(N-Boc-amino)-1,6-heptanedioic acid

- Specification
  - Storage
    
    Please store the product under the recommended conditions in the Certificate of Analysis.
    
    Shipping
    
    Room temperature in continental US; may vary elsewhere.
    
    IUPAC Name
    
    4-[(2-methylpropan-2-yl)oxycarbonylamino]heptanedioic acid
- Properties
  - InChI Key
    
    CVMSTDAWIAVWJN-UHFFFAOYSA-N
    
    InChI
    
    InChI=1S/C12H21NO6/c1-12(2,3)19-11(18)13-8(4-6-9(14)15)5-7-10(16)17/h8H,4-7H2,1-3H3,(H,13,18)(H,14,15)(H,16,17)
    
    Canonical SMILES
    
    CC(C)(C)OC(=O)NC(CCC(=O)O)CCC(=O)O
- Reference Reading
  - 1. Efficient synthesis of enantiopure pyrrolizidinone amino acid
    
    Evelyne Dietrich, William D Lubell J Org Chem. 2003 Sep 5;68(18):6988-96. doi: 10.1021/jo034739d.
    
    Enantiopure (3S,5R,8S)-3-[N-(Boc)amino]-1-azabicyclo[3.3.0]octan-2-one 8-carboxylic acid (1) was synthesized in nine steps and 16% overall yield from aspartate beta-aldehyde 7. Carbene-catalyzed acyloin condensation of 7, followed by acetylation and samarium iodide reduction, gave linear precursor (2S,7S)-alpha,omega-diamino-4-oxosuberate 11, which was converted to N-(Boc)aminopyrrolizidin-2-one carboxylic acid 1 by a reductive amination/lactam cyclization sequence. X-ray analysis of (3S,5R,8S)-methyl N-(Boc)aminopyrrolizidin-2-one carboxylate 21 showed that its internal backbone dihedral angles (psi = -149 degrees, phi = -49 degrees ) were in good agreement with the ideal values for a type II' beta-turn. Proton NMR experiments on N'-methyl-N-(Boc)aminopyrrolizidin-2-one carboxamide 23 demonstrated significantly different NH chemical displacements and temperature coefficients suggestive of solvent shielded and exposed hydrogens indicative of a turn conformation. Because pyrrolizidinone amino acids can serve as conformationally rigid dipeptide surrogates, this synthesis should facilitate their application in the exploration of conformation-activity relationships of various biologically active peptides.

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