(2S)-3-amino-2-{[(tert-butoxy)carbonyl]amino}propanoic acid

• ChemBase ID: 38585
• Molecular Formular: C8H16N2O4
• Molecular Mass: 204.22364
• Monoisotopic Mass: 204.111007
• SMILES: [C@H](CN)(C(=O)O)NC(=O)OC(C)(C)C
• Canonical SMILES: NC[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C8H16N2O4/c1-8(2,3)14-7(13)10-5(4-9)6(11)12/h5H,4,9H2,1-3H3,(H,10,13)(H,11,12)/t5-/m0/s1
• InChIKey: KRJLRVZLNABMAT-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-amino-2-{[(tert-butoxy)carbonyl]amino}propanoic acid
• IUPAC Traditional name: (2S)-3-amino-2-[(tert-butoxycarbonyl)amino]propanoic acid
• Synonyms: Boc-Dap-OH; 3-Amino-N-Boc-L-alanine; N(alpha)-Boc-L-2,3-diaminopropionic acid; Boc-L-2,3-Diaminopropionic acid; Boc-Dap-OH; (S)-2-[(tert-Butoxycarbonyl)amino]-3-aminopropionic acid; (S)-3-Amino-2-(tert-butoxycarbonyl)aminopropionic acid; Nα-BOC-(S)-β-aminoalanine; Nα-Boc-L-β-aminoalanine; N2-(tert-Butoxycarbonyl)-(S)-2,3-diaminopropionic acid; N2-tert-Butoxycarbonyl-L-2,3-diaminopropionic acid; Boc-Dap-OH; Boc-Dpr-OH; (S)-3-Amino-2-(tert-butoxycarbonylamino)propanoic acid; 3-Amino-(tert-butoxycarbonyl)-L-alanine; Nα-Boc-L-2,3-diaminopropionic acid; (N-Boc-β-amino)-Ala-OH; N(α)-Boc-L-2,3-二氨丙酸; (S)-3-氨基-2-(叔丁氧羰基氨基)丙酸; 3-氨基-(叔丁氧羰基)-L-丙氨酸; Nα-Boc-L-2,3-二氨基丙酸; (N-Boc-β-氨基)-丙氨酸

Database IDs

• CAS Number: 73259-81-1
• MDL Number: MFCD00236843
• Beilstein Number: 4182136
• PubChem SID: 161001892; 24849398; 24884604
• PubChem CID: 2755946

CALCULATED PROPERTIES

• Acid pKa: 3.3544285
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.505428
• LogD (pH = 7.4): -2.5082457
• Log P: -2.5038223
• Molar Refractivity: 48.5715 cm^3
• Polarizability: 19.523464 Å^3
• Polar Surface Area: 101.65 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 210 °C (dec.); ca 210°C dec.
• Optical Rotation: [α]20/D +5.5±1°, c = 1% in methanol: water (1:1); -14 (c=1 in water)

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (TLC); 97%
• Impurities: ~3% water
• Empirical Formula (Hill Notation): C8H16N2O4

DETAILS

Sigma Aldrich - 15402

Other Notes
Monoprotected derivative of DAP; used e.g. in the synthesis of glucosamine synthase inhibitors,6,7 a myosin kinase inhibitor.8 Preparation of peptides with metal complexing groups.9
Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Protein assembly directed by synthetic molecular recognition motifs1
• Solid phase synthesis of gramicidin S cyclic analogs with antibiotic and hemolytic activities2
• Synthesis of HCV protease inhibitor modified analogs3
• Solid phase synthesis of peptidic V1a receptor agonists4
• Directed peptide assembly at lipid-water interface5

Sigma Aldrich - 662836

Packaging
1 g in glass bottle
Application
Reactant for:
• Protein assembly directed by synthetic molecular recognition motifs1
• Solid phase synthesis of gramicidin S cyclic analogs with antibiotic and hemolytic activities2
• Synthesis of HCV protease inhibitor modified analogs3
• Solid phase synthesis of peptidic V1a receptor agonists4
• Directed peptide assembly at lipid-water interface5