(3S,4S)-3-hydroxy-4-[(2S)-2-[(3S,4S)-3-hydroxy-6-methyl-4-[(2S)-3-methyl-2-[(2S)-3-methyl-2-(3-methylbutanamido)butanamido]butanamido]heptanamido]propanamido]-6-methylheptanoic acid

• ChemBase ID: 105967
• Molecular Formular: C34H63N5O9
• Molecular Mass: 685.89212
• Monoisotopic Mass: 685.46257862
• SMILES: O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(=O)N[C@H](C(=O)N[C@H]([C@@H](O)CC(=O)O)CC(C)C)C)C(C)C)C(C)C)CC(C)C
• Canonical SMILES: CC(C[C@@H]([C@H](CC(=O)N[C@H](C(=O)N[C@H]([C@H](CC(=O)O)O)CC(C)C)C)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C)C
• InChI: InChI=1S/C34H63N5O9/c1-17(2)12-23(37-33(47)31(21(9)10)39-34(48)30(20(7)8)38-27(42)14-19(5)6)25(40)15-28(43)35-22(11)32(46)36-24(13-18(3)4)26(41)16-29(44)45/h17-26,30-31,40-41H,12-16H2,1-11H3,(H,35,43)(H,36,46)(H,37,47)(H,38,42)(H,39,48)(H,44,45)/t22-,23-,24-,25-,26-,30-,31-/m0/s1
• InChIKey: FAXGPCHRFPCXOO-LXTPJMTPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S)-3-hydroxy-4-[(2S)-2-[(3S,4S)-3-hydroxy-6-methyl-4-[(2S)-3-methyl-2-[(2S)-3-methyl-2-(3-methylbutanamido)butanamido]butanamido]heptanamido]propanamido]-6-methylheptanoic acid
• IUPAC Traditional name: pepstatin
• Synonyms: Pepstatin A; Isoval-Val-Val-Sta-Ala-Sta; PEPSTATIN A; Pepstatin A; Pepstatin; 胃酶抑素 A

Database IDs

• CAS Number: 26305-03-3
• EC Number: 247-600-0
• MDL Number: MFCD00060740
• Beilstein Number: 2201362
• PubChem SID: 162093877; 24898620; 24887125; 24898519
• PubChem CID: 5478883
• Chemspider ID: 4586014
• KEGG ID: D03818
• Wikipedia Title: Pepstatin

CALCULATED PROPERTIES

• Acid pKa: 4.3156843
• H Acceptors: 9
• H Donor: 8
• LogD (pH = 5.5): 0.50849324
• LogD (pH = 7.4): -1.2331531
• Log P: 1.7183708
• Molar Refractivity: 179.4192 cm^3
• Polarizability: 71.26343 Å^3
• Polar Surface Area: 223.26 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: soluble1-2 mg/mL (with heat up to 60 °C)
• Melting Point: 233 °C (dec.)(lit.); 235-237°C
• Optical Rotation: [α]20/D -90°, c = 0.3 in methanol

Safety Information

• Storage Condition: 0°C, Protect from light
• RTECS: SC6155000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥75% (HPLC)
• Biological Source: microbial
• Empirical Formula (Hill Notation): C34H63N5O9

DETAILS

MP Biomedicals - 02195368

Synthetic
Inhibitor for pepsin, renin, cathepsin D, and other acid proteases.

Sigma Aldrich - P5318

Application
Can be used in conjunction with E64-d and Leupeptin A to inhibit the degradation of autophagic cargo inside autophagosomes. For this application, the working concentration is typically between 1-10 μM.
Preparation Note
胃酶抑素可以 1mg/ml 的浓度溶于含 10% (v/v) 乙酸的甲醇（9:1 甲醇:乙酸）中。乙酸的添加对于该多肽在甲醇或 DMSO 中的溶解可能是必需的。它能以 1 至 2mg/ml 的浓度溶于乙醇，但完全溶解需要加热。胃酶抑素 A 的溶液可加热至高达 60°C，而不会发生任何降解。 1mg/ml 的储存液在 4°C 下可稳定至少一周。1mM 的甲醇或 DMSO 溶液在 -20°C 下可稳定数月。如果溶液逐渐变为深黄色，说明试剂正在发生水解。 工作浓度为 1μM 时，可在室温下稳定至少一天。
Biochem/physiol Actions
胃酶抑素 A 是酸性蛋白酶（天冬氨酰基肽酶）的抑制剂。它可与蛋白酶如胃蛋白酶、肾素、组织蛋白酶 D、牛凝乳酶和蛋白酶 B（黑曲霉）形成 1:1 的复合物。该抑制剂具有高度的选择性，不会抑制硫醇蛋白酶、中性蛋白酶或丝氨酸蛋白酶。可溶性 γ-分泌酶和逆转录病毒蛋白酶也可被胃酶抑素 A 抑制。它已用于鉴定多种来源的蛋白酶。

Sigma Aldrich - P4265

Application
Can be used in conjunction with E64-d and Leupeptin A to inhibit the degradation of autophagic cargo inside autophagosomes. For this application, the working concentration is typically between 1-10 μM.
Preparation Note
胃酶抑素可以 1mg/ml 的浓度溶于含 10% (v/v) 乙酸的甲醇（9:1 甲醇:乙酸）中。乙酸的添加对于该多肽在甲醇或 DMSO 中的溶解可能是必需的。它能以 1 至 2mg/ml 的浓度溶于乙醇，但完全溶解需要加热。胃酶抑素 A 的溶液可加热至高达 60°C，而不会发生任何降解。 1mg/ml 的储存液在 4°C 下可稳定至少一周。1mM 的甲醇或 DMSO 溶液在 -20°C 下可稳定数月。如果溶液逐渐变为深黄色，说明试剂正在发生水解。 工作浓度为 1μM 时，可在室温下稳定至少一天。
Biochem/physiol Actions
胃酶抑素 A 是酸性蛋白酶（天冬氨酰基肽酶）的抑制剂。它可与蛋白酶如胃蛋白酶、肾素、组织蛋白酶 D、牛凝乳酶和蛋白酶 B（黑曲霉）形成 1:1 的复合物。该抑制剂具有高度的选择性，不会抑制硫醇蛋白酶、中性蛋白酶或丝氨酸蛋白酶。可溶性 γ-分泌酶和逆转录病毒蛋白酶也可被胃酶抑素 A 抑制。它已用于鉴定多种来源的蛋白酶。

Sigma Aldrich - 77170

Application
Can be used in conjunction with E64-d and Leupeptin A to inhibit the degradation of autophagic cargo inside autophagosomes. For this application, the working concentration is typically between 1-10 μM.
Other Notes
Strong inhibitor of acid proteases - pepsin, cathepsin D, renin1,2,3
Preparation Note
Pepstatin can be dissolved at 1 mg/ml in 10% (v/v) acetic acid in methanol (9:1 methanol:acetic acid). The inclusion of acetic acid may be necessary to dissolve this peptide in methanol or DMSO. It has been dissolved at 1 to 2 mg/ml in ethanol, but heat may be required for complete dissolution. Solutions of Pepstatin A can be heated as high as 60 °C without any decomposition of the peptide. Stock solutions at 1 mg/ml are stable at least a week at 4 °C. A 1 mM solution in methanol or DMSO is stable for months at -20 °C. If solutions become darker yellow, the reagent is hydrolyzing.A working concentration of 1 μM is stable for at least one day at room temperature.
Unit Definition
1 U corresponds to the amount of inhibitor which reduces the activity of pepsin by 1 U (1 U corresponds to the amount of enzyme which increases the absorbance at 280 nm by 0.001 per minute at pH 2.0 and 37°C (Hemoglobin, Fluka-No. 51290, as substrate, in an endvolume of 16 ml)); 10′000 absorbance-U as described above are equivalent to ～1 Bergmeyer-U (when 1 pepsin-U is the amount of enzyme which hydrolyzes 1 μmol acetyl-L-phenylalanyl-3,5-diiodo-L-tyrosin per minute at pH 2.0 and 37°C)
Biochem/physiol Actions
Pepstatin A is an inhibitor of acid proteases (aspartyl peptidases). It forms a 1:1 complex with proteases such as pepsin, renin, cathepsin D, bovine chymosin, and protease B (Aspergillus niger). The inhibitor is highly selective and does not inhibit thiol proteases, neutral proteases, or serine proteases. Solubilized γ-secretase and retroviral protease are also inhibited by Pepstatin A. It has been used to characterize proteases from several sources.

Sigma Aldrich - 360325

Preparation Note
Pepstatin can be dissolved at 1 mg/ml in 10% (v/v) acetic acid in methanol (9:1 methanol:acetic acid). The inclusion of acetic acid may be necessary to dissolve this peptide in methanol or DMSO. It has been dissolved at 1 to 2 mg/ml in ethanol, but heat may be required for complete dissolution. Solutions of Pepstatin A can be heated as high as 60 °C without any decomposition of the peptide. Stock solutions at 1 mg/ml are stable at least a week at 4 °C. A 1 mM solution in methanol or DMSO is stable for months at -20 °C. If solutions become darker yellow, the reagent is hydrolyzing.A working concentration of 1 μM is stable for at least one day at room temperature.
Biochem/physiol Actions
Pepstatin A is an inhibitor of acid proteases (aspartyl peptidases). It forms a 1:1 complex with proteases such as pepsin, renin, cathepsin D, bovine chymosin, and protease B (Aspergillus niger). The inhibitor is highly selective and does not inhibit thiol proteases, neutral proteases, or serine proteases. Solubilized γ-secretase and retroviral protease are also inhibited by Pepstatin A. It has been used to characterize proteases from several sources.

REFERENCES

• Umezawa, H., et al., J. Antibiot., 23: 259 (1970).
• Lazar, J., et al., Biochem. Pharmac., 23: 2776 (1974).