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

• ChemBase ID: 152365
• Molecular Formular: C12H18N2O6
• Molecular Mass: 286.28112
• Monoisotopic Mass: 286.11648631
• SMILES: C[C@@H](C(=O)ON1C(=O)CCC1=O)NC(=O)OC(C)(C)C
• Canonical SMILES: C[C@@H](C(=O)ON1C(=O)CCC1=O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C12H18N2O6/c1-7(13-11(18)19-12(2,3)4)10(17)20-14-8(15)5-6-9(14)16/h7H,5-6H2,1-4H3,(H,13,18)/t7-/m0/s1
• InChIKey: COMUWNFVTWKSDT-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl (2S)-2-{[(tert-butoxy)carbonyl]amino}propanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl (2S)-2-[(tert-butoxycarbonyl)amino]propanoate
• Synonyms: Boc-L-alanine N-succinimidyl ester; Boc-L-alanine hydroxysuccinimide ester; Boc-Ala-OSu; Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate; Boc-L-丙氨酸-N-丁二酰亚胺酯; Boc-L-丙氨酸丁二酰亚胺酯

Database IDs

• CAS Number: 3392-05-0
• EC Number: 222-229-7
• MDL Number: MFCD00065974
• Beilstein Number: 3560476
• PubChem SID: 162246510; 24849382
• PubChem CID: 11011585

CALCULATED PROPERTIES

• Acid pKa: 13.084517
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.28297144
• LogD (pH = 7.4): 0.28297067
• Log P: 0.28297147
• Molar Refractivity: 65.9241 cm^3
• Polarizability: 26.277895 Å^3
• Polar Surface Area: 102.01 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 161-163 °C
• Optical Rotation: [α]20/D -52±1°, c = 2.5% in dioxane

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 95+%
• Empirical Formula (Hill Notation): C12H18N2O6

DETAILS

Sigma Aldrich - 15385

Packaging
5 g in glass bottle
Application
Reactant involved in synthesis of:
• Muramyldipeptide analogs via solid-phase synthesis1
• Microcin C analogs for use as antibacterials2
• Lipid I and nucleoside diphosphate peptide derivatives via N-methylimidazolium chloride catalyzed coupling3
• N-Protected dipeptide acids4
• Free and peptide-bound glycated amino acids for studies of interactions with human Caco-2 interstinal epithelial cell apical membrane transport proteins5
• 7-Substituted camptothecin conjugates with RGD-peptides as avβ3 integrin ligands6