(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-carbamoylbutanoic acid

• ChemBase ID: 59951
• Molecular Formular: C10H18N2O5
• Molecular Mass: 246.26032
• Monoisotopic Mass: 246.12157169
• SMILES: C(=O)(N[C@H](C(=O)O)CCC(=O)N)OC(C)(C)C
• Canonical SMILES: NC(=O)CC[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C10H18N2O5/c1-10(2,3)17-9(16)12-6(8(14)15)4-5-7(11)13/h6H,4-5H2,1-3H3,(H2,11,13)(H,12,16)(H,14,15)/t6-/m0/s1
• InChIKey: VVNYDCGZZSTUBC-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-carbamoylbutanoic acid
• IUPAC Traditional name: (2S)-2-[(tert-butoxycarbonyl)amino]-4-carbamoylbutanoic acid
• Synonyms: Nα-(tert-Butoxycarbonyl)-L-glutamine; Boc-L-glutamine; Boc-Gln-OH; N-α-t-BOC-L-GLUTAMINE; Boc-D-Gln-OH; N(alpha)-tert-Butoxycarbonyl-D-glutamine; N(alpha)-Boc-D-glutamine; Boc-Gln-OH; N(alpha)-tert-Butoxycarbonyl-L-glutamine; N(alpha)-Boc-L-glutamine; (S)-5-Amino-2-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid; (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-carbamoylbutanoic acid; N2-[(1,1-Dimethylethoxy)carbonyl]-L-glutamine; N2-Carboxy-glutamine N-tert-Butyl Ester; (S)-2-[(tert-Butoxycarbonyl)amino]-4-carbamoylbutanoic Acid; BOC-glutamine; NSC 334370; tert-Butoxycarbonyl-L-glutamine; N~2~-(tert-butoxycarbonyl)-L-glutamine; Nα-(叔丁氧羰基)-L-谷氨酰胺; Boc-L-谷氨酰胺; N(α)-Boc-D-谷氨酸; N(α)-Boc-L-谷氨酰胺

Database IDs

• CAS Number: 13726-85-7; 61348-28-5
• EC Number: 237-296-8
• MDL Number: MFCD00038158; MFCD00065571
• Beilstein Number: 1981311; 2127805
• PubChem SID: 162064714; 24865570
• PubChem CID: 83687

CALCULATED PROPERTIES

• Acid pKa: 3.864043
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.8870786
• LogD (pH = 7.4): -3.4785044
• Log P: -0.24670725
• Molar Refractivity: 57.9829 cm^3
• Polarizability: 22.953348 Å^3
• Polar Surface Area: 118.72 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 113-116 °C (dec.)(lit.); 117-119°C; 118-120°C
• Optical Rotation: [α]20/D -3.4±0.5°, c = 2% in ethanol; [α]20/D -3.5°, c = 1 in ethanol; +3.5 (c=2 in ethanol); -3.5 (c=2 in ethanol)
• Hydrophobicity(logP): -0.636

Safety Information

• Storage Condition: 0°C
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false; 否; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CCR2(1231)

Product Information

• Purity: ≥99.0% (T); 95%; 98%; 98+%
• Grade: puriss.
• Linear Formula: NH2COCH2CH2CH(COOH)NHCOOC(CH3)3

DETAILS

MP Biomedicals - 02101069

Crystalline

Sigma Aldrich - 408441

Packaging
5, 25 g in glass bottle

Toronto Research Chemicals - B690430

Protected Glutamine.

REFERENCES

• Ohshiro, T., et al.: App. Microbiol. Biotechnol., 48, 546 (1997)
• Fox, D., et al.: J. Med. Chem., 45, 360 (1997)