(3S,4S)-4-{[(tert-butoxy)carbonyl]amino}-3-hydroxy-6-methylheptanoic acid

• ChemBase ID: 39167
• Molecular Formular: C13H25NO5
• Molecular Mass: 275.3413
• Monoisotopic Mass: 275.17327291
• SMILES: C([C@@H]([C@H](CC(C)C)NC(=O)OC(C)(C)C)O)C(=O)O
• Canonical SMILES: O[C@H]([C@@H](NC(=O)OC(C)(C)C)CC(C)C)CC(=O)O
• InChI: InChI=1S/C13H25NO5/c1-8(2)6-9(10(15)7-11(16)17)14-12(18)19-13(3,4)5/h8-10,15H,6-7H2,1-5H3,(H,14,18)(H,16,17)/t9-,10-/m0/s1
• InChIKey: KJIQRHBVNGRPCO-UWVGGRQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S)-4-{[(tert-butoxy)carbonyl]amino}-3-hydroxy-6-methylheptanoic acid
• IUPAC Traditional name: (3S,4S)-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-6-methylheptanoic acid
• Synonyms: (3S,4S)-4-(Boc-amino)-3-hydroxy-6-methylheptanoic acid; Boc-statine; Boc-Sta(3S,4S)-OH; Boc-Sta-OH

Database IDs

• CAS Number: 58521-49-6
• MDL Number: MFCD00063180
• Beilstein Number: 3550534
• PubChem SID: 24849393; 161002474
• PubChem CID: 2755962

CALCULATED PROPERTIES

• Acid pKa: 4.589537
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.6622254
• LogD (pH = 7.4): -1.1132438
• Log P: 1.6219848
• Molar Refractivity: 69.6307 cm^3
• Polarizability: 27.790068 Å^3
• Polar Surface Area: 95.86 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 119-122 °C
• Optical Rotation: [α]20/D -41±2°, c = 0.5% in methanol

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ~95% (sum of enantiomers, HPLC)
• Empirical Formula (Hill Notation): C13H25NO5

DETAILS

Sigma Aldrich - 15397

Application
(3S,4S)-Statine is often used as a non-hydrolyzable isosteric replacement for a dipeptide unit in design of synthetic peptide protease inhibitors.1
Other Notes
(3S,4S)-Statine is a novel amino acid of pepstatin, a low molecular weight inhibitor of acid proteases2,3