(2S)-N-[(1S)-1-{[(2S)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-3-methylbutyl]-2-acetamido-4-methylpentanamide; trifluoroacetic acid

• ChemBase编号: 133096
• 分子式: C22H39F3N6O6
• 平均质量: 540.5768696
• 单一同位素质量: 540.28831766
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C=O)NC(=O)C.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.O=C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(C)C)CC(C)C)CCCNC(=N)N
• InChI: InChI=1S/C20H38N6O4.C2HF3O2/c1-12(2)9-16(24-14(5)28)19(30)26-17(10-13(3)4)18(29)25-15(11-27)7-6-8-23-20(21)22;3-2(4,5)1(6)7/h11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23);(H,6,7)/t15-,16-,17-;/m0./s1
• InChIKey: WUHGBZVQELGOMH-FRKSIBALSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-N-[(1S)-1-{[(2S)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-3-methylbutyl]-2-acetamido-4-methylpentanamide; trifluoroacetic acid
• IUPAC传统名: (2S)-N-[(1S)-1-{[(2S)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-3-methylbutyl]-2-acetamido-4-methylpentanamide; trifluoroacetic acid
• 别名: 亮抑酶肽 三氟乙酸盐; Acetyl-Leu-Leu-Arg-al 三氟乙酸盐; Leupeptin trifluoroacetate salt

登记号

• CAS号: 147385-61-3
• MDL号: MFCD00133458
• PubChem SID: 162227373
• PubChem CID: 44120072

理论计算性质

• Acid pKa: 12.4916725
• 质子受体: 7
• 质子供体: 6
• LogD (pH = 5.5): -2.8089597
• LogD (pH = 7.4): -2.8059762
• Log P: -0.7743988
• 摩尔折射率: 124.3835 cm^3
• 极化性: 44.33278 Å^3
• 极化表面积: 166.27 Å^2
• 可自由旋转的化学键: 15
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: H2O: soluble10 mM (Solutions are stable only a few hours. Stock solutions are stable up to 6 months at -20 °C.)

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: ≥90% (HPLC)
• 生物来源: microbial

详细说明

Sigma Aldrich - L2023

Analysis Note
由于三种形式在溶液中达到平衡，亮抑酶肽可在 HPLC 上形成多个峰。通过三个主峰测定纯度。主要的杂质肽为外消旋亮抑酶肽。
Biochem/physiol Actions
Inhibitor of serine and cysteine proteases. Inhibits plasmin, trypsin, papain, calpain, and cathepsin B. Does not inhibit pepsin, cathepsins A and D, thrombin, or α-chymotrypsin. Effective concentration 10-100 μM. There have been numerous studies using leupeptin to protect against hearing loss caused by acoustic overstimulation or the ototoxic antibiotic gentamicin.1 (Loss of cochlear hair cells is believed to be mediated by calpain.)