2,5-dioxopyrrolidin-1-yl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoate

• ChemBase ID: 152127
• Molecular Formular: C18H22N2O7
• Molecular Mass: 378.37648
• Monoisotopic Mass: 378.14270105
• SMILES: CC(C)(C)OC(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C([C@H](Cc1ccc(cc1)O)NC(=O)OC(C)(C)C)ON1C(=O)CCC1=O
• InChI: InChI=1S/C18H22N2O7/c1-18(2,3)26-17(25)19-13(10-11-4-6-12(21)7-5-11)16(24)27-20-14(22)8-9-15(20)23/h4-7,13,21H,8-10H2,1-3H3,(H,19,25)/t13-/m0/s1
• InChIKey: NZUDTLHVKHXJJJ-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate
• Synonyms: Boc-L-tyrosine hydroxysuccinimide ester; Boc-Tyr-OSu; Boc-L-酪氨酸羟基琥珀酰亚胺酯

Database IDs

• CAS Number: 20866-56-2
• MDL Number: MFCD00037910
• Beilstein Number: 1557147
• PubChem SID: 24849506; 162246272
• PubChem CID: 12790906

CALCULATED PROPERTIES

• Acid pKa: 9.503784
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6356897
• LogD (pH = 7.4): 1.632346
• Log P: 1.6357325
• Molar Refractivity: 92.524 cm^3
• Polarizability: 36.403374 Å^3
• Polar Surface Area: 122.24 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~190 °C (dec.)
• Optical Rotation: [α]20/D -13±1°, c = 1% 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: ≥99.0% (N)
• Empirical Formula (Hill Notation): C18H22N2O7

DETAILS

Sigma Aldrich - 15525

Other Notes
Reagent used in a rapid method for iodotyrosylation of peptides.; This method is equal to that of Bolton-Hunter but has the additional advantage that the derivatized peptide is readily deblocked to form a radiolabelled product with the same net charge as the starting material1
Packaging
5 g in glass bottle