2,5-dioxopyrrolidin-1-yl (2S)-6-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}hexanoate

• ChemBase ID: 139287
• Molecular Formular: C23H31N3O8
• Molecular Mass: 477.50754
• Monoisotopic Mass: 477.21111497
• SMILES: CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(OCc1ccccc1)NCCCC[C@@H](C(=O)ON1C(=O)CCC1=O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C23H31N3O8/c1-23(2,3)33-22(31)25-17(20(29)34-26-18(27)12-13-19(26)28)11-7-8-14-24-21(30)32-15-16-9-5-4-6-10-16/h4-6,9-10,17H,7-8,11-15H2,1-3H3,(H,24,30)(H,25,31)/t17-/m0/s1
• InChIKey: YWLICOCXPNQJPC-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl (2S)-6-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}hexanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl (2S)-6-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]hexanoate
• Synonyms: Nα-Boc-Nε-Cbz-L-lysine N-hydroxysuccinimide ester; Nα-Boc-Nε-Z-L-lysine hydroxysuccinimide ester; Nε-Z-Nα-Boc-L-lysine hydroxysuccinimide ester; Boc-Lys(Z)-OSu; Nα-Boc-Nε-Cbz-L-赖氨酸 N-羟基琥珀酰亚胺酯; Nα-Boc-Nε-Z-L-赖氨酸羟基琥珀酰亚胺酯; Nε-苄氧羰基-Nα-叔丁氧羰基-L-赖氨酸羟基琥珀酰亚胺酯

Database IDs

• CAS Number: 34404-36-9
• EC Number: 251-999-7
• MDL Number: MFCD00037915
• Beilstein Number: 1559393
• PubChem SID: 162233535; 24849529
• PubChem CID: 12686578

CALCULATED PROPERTIES

• Acid pKa: 13.074343
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.3136816
• LogD (pH = 7.4): 2.313681
• Log P: 2.3136816
• Molar Refractivity: 118.9163 cm^3
• Polarizability: 46.90659 Å^3
• Polar Surface Area: 140.34 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 108-117 °C
• Optical Rotation: [α]20/D -20.5±1.5°, c = 2% in dioxane

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ~80%
• Empirical Formula (Hill Notation): C23H31N3O8

DETAILS

Sigma Aldrich - B3256

Application
Reactant involved in:
• Cellular labeling and tumor MRI as a bimodal lipidic contrast agent1
• Synthesis of improved peptide prodrugs 5-ALA for photodynamic therapy2
• Design of high affinity peptide conjugates as markers for small peptide transporter PEPT1 (SLC15A1)3
• Preparation of human growth hormone derivatives containing PEG groups4
• Enantiodivergent asymmetric cyclization5
• Solid-phase synthesis of peptide-cationic steroid conjugates for antibacterial screening6

Sigma Aldrich - 15541

Packaging
5, 25 g in poly bottle
Application
Reactant involved in:
• Cellular labeling and tumor MRI as a bimodal lipidic contrast agent1
• Synthesis of improved peptide prodrugs 5-ALA for photodynamic therapy2
• Design of high affinity peptide conjugates as markers for small peptide transporter PEPT1 (SLC15A1)3
• Preparation of human growth hormone derivatives containing PEG groups4
• Enantiodivergent asymmetric cyclization5
• Solid-phase synthesis of peptide-cationic steroid conjugates for antibacterial screening6