67655-94-1

Basic information

• Product Name: AMASTATIN
• Synonyms: (2S,3R)-3-AMINO-2-HYDROXY-5-METHYLHEXANOYL-VAL-VAL-ASP-OH;[(2S,3R)-3-AMINO-2-HYDROXY-5-METHYLHEXANOYL]-L-VALYL-L-VALYL-L-ASPARTIC ACID;AMASTATIN, STREPTOMYCES SPECIES;AMASTATIN;(AMINO-2-HYDROXY-5-METHYL-HEXANOYL)-L-VALYL-L-VALYL-L-ASPARTIC ACID;N-[(2S,3R)-3-AMINO-2-HYDROXY-5-METHYLHEXANOYL]-L-VALYL-L-VALYL-L-ASPARTIC ACID;l-asparticacid,n-(n-(3-amino-2-hydroxy-5-methyl-1-oxohexyl)-l-valyl)-l-valyl);s*))-(s-(r*
• CAS NO: 67655-94-1
• Molecular Formula: C₂₁H₃₈N₄O₈
• Molecular Weight: 474.55
• Product Categories: inhibitor
• Mol File: 67655-94-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 795℃
• Flash Point: 435℃
• Appearance: /
• Density: 1.228
• Vapor Pressure: 3.14E-29mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: AMASTATIN(CAS DataBase Reference)
• NIST Chemistry Reference: AMASTATIN(67655-94-1)
• EPA Substance Registry System: AMASTATIN(67655-94-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 67655-94-1(Hazardous Substances Data)

Usage

Description

Amastatin is a tetrapeptide consisting of (2S,3R)-3-amino-2-hydroxy-5-methylhexanoyl, L-valyl, L-valyl, and L-aspartic acid units joined in sequence. It is a naturally occurring bioactive compound with potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
Amastatin is used as a pharmaceutical agent for its potential therapeutic properties. It has been found to exhibit inhibitory effects on certain enzymes and pathways, making it a promising candidate for the development of drugs targeting specific diseases.
Used in Research Applications:
Amastatin is used as a research tool for studying the mechanisms of action and potential applications of bioactive peptides. Its unique structure and properties allow researchers to investigate its interactions with biological systems and explore its potential as a therapeutic agent.
Used in Drug Development:
Amastatin is used in drug development as a lead compound for the design and synthesis of new drugs. Its unique structure and biological activity provide a foundation for the development of novel therapeutic agents with improved efficacy and selectivity.

InChI:InChI=1/C21H38N4O8/c1-9(2)7-12(22)17(28)20(31)25-16(11(5)6)19(30)24-15(10(3)4)18(29)23-13(21(32)33)8-14(26)27/h9-13,15-17,28H,7-8,22H2,1-6H3,(H,23,29)(H,24,30)(H,25,31)(H,26,27)(H,32,33)/t12-,13+,15+,16+,17+/m1/s1

Synthetic route

(2S,3R)-<3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoyl>-L-valyl-L-valyl-aspartic Acid Dibenzyl Ester (73397-34-9) → amastatin (67655-94-1)

Conditions	Yield
With palladium on activated charcoal; hydrogen; trifluoroacetic acid 1.) room temperature, 30 min 2.) methanol, 24 h; Yield given. Multistep reaction;

(S)-2-{(S)-2-[(S)-2-((2S,3R)-3-Benzyloxycarbonylamino-2-hydroxy-5-methyl-hexanoylamino)-3-methyl-butyrylamino]-3-methyl-butyrylamino}-succinic acid dibenzyl ester → amastatin (67655-94-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal

t-Boc-L-valine (13734-41-3) → amastatin (67655-94-1)

Conditions	Yield
Multi-step reaction with 6 steps 1: DCC, HOBt, Et3N 2: TFA 3: DCC, HOBt, Et3N 4: TFA 5: DCC, HOBt, Et3N 6: H2 / Pd-C View Scheme
Multi-step reaction with 4 steps 1: 80 percent / triethylamine, DCC, HOBt / CH2Cl2 / 5 °C 2: 1.) HCl, 2.) triethylamine, DCC, HOBt 3: 1.) hydrochloric acid, 2.) triethylamine, DCC, HOBt / 1.) dioxane, 30 min, 25 deg C 2.) methylene chloride 4: 1.) TFA, 2.) H2, Pd/C / 1.) room temperature, 30 min 2.) methanol, 24 h View Scheme

Boc-Val-Asp(OBzl)-OBzl (70853-19-9) → amastatin (67655-94-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: TFA 2: DCC, HOBt, Et3N 3: TFA 4: DCC, HOBt, Et3N 5: H2 / Pd-C View Scheme
Multi-step reaction with 3 steps 1: 1.) HCl, 2.) triethylamine, DCC, HOBt 2: 1.) hydrochloric acid, 2.) triethylamine, DCC, HOBt / 1.) dioxane, 30 min, 25 deg C 2.) methylene chloride 3: 1.) TFA, 2.) H2, Pd/C / 1.) room temperature, 30 min 2.) methanol, 24 h View Scheme

<(tert-Butyloxy)carbonyl>-L-valyl-L-valyl-L-aspartic Acid Dibenzyl Ester (70853-22-4) → amastatin (67655-94-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: TFA 2: DCC, HOBt, Et3N 3: H2 / Pd-C View Scheme
Multi-step reaction with 2 steps 1: 1.) hydrochloric acid, 2.) triethylamine, DCC, HOBt / 1.) dioxane, 30 min, 25 deg C 2.) methylene chloride 2: 1.) TFA, 2.) H2, Pd/C / 1.) room temperature, 30 min 2.) methanol, 24 h View Scheme

Val-Asp(OBzl)-OBzl (70853-20-2) → amastatin (67655-94-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: DCC, HOBt, Et3N 2: TFA 3: DCC, HOBt, Et3N 4: H2 / Pd-C View Scheme

Val-Val-Asp(OBzl)-OBzl (70853-23-5) → amastatin (67655-94-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: DCC, HOBt, Et3N 2: H2 / Pd-C View Scheme

(R)-4-methyl-1-oxopentane-2-benzylcarbamate (70853-26-8) → amastatin (67655-94-1)

Conditions

Yield

Multi-step reaction with 5 steps 1: 1.) NaHSO3 / 1.) 5 deg C, overnight, 2.) ethyl acetate, water, room temp., 4 h 2: 90 percent / concentrated HCl / dioxane / 12 h / Heating 3: 73 percent / triethylamine / H2O; dioxane / 25 °C 4: 1.) hydrochloric acid, 2.) triethylamine, DCC, HOBt / 1.) dioxane, 30 min, 25 deg C 2.) methylene chloride 5: 1.) TFA, 2.) H2, Pd/C / 1.) room temperature, 30 min 2.) methanol, 24 h View Scheme

[(S)-1-((S)-Cyano-hydroxy-methyl)-3-methyl-butyl]-carbamic acid benzyl ester (63219-62-5, 73397-23-6, 73397-24-7, 106868-70-6, 106868-79-5) → amastatin (67655-94-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / concentrated HCl / dioxane / 12 h / Heating 2: 73 percent / triethylamine / H2O; dioxane / 25 °C 3: 1.) hydrochloric acid, 2.) triethylamine, DCC, HOBt / 1.) dioxane, 30 min, 25 deg C 2.) methylene chloride 4: 1.) TFA, 2.) H2, Pd/C / 1.) room temperature, 30 min 2.) methanol, 24 h View Scheme

(2RS,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid (62023-30-7, 70853-11-1, 70853-17-7, 73397-20-3, 73397-21-4, 75556-30-8) → amastatin (67655-94-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 73 percent / triethylamine / H2O; dioxane / 25 °C 2: 1.) hydrochloric acid, 2.) triethylamine, DCC, HOBt / 1.) dioxane, 30 min, 25 deg C 2.) methylene chloride 3: 1.) TFA, 2.) H2, Pd/C / 1.) room temperature, 30 min 2.) methanol, 24 h View Scheme

(2RS,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid (73397-25-8, 73397-26-9, 73397-27-0, 73397-28-1, 77119-88-1) → amastatin (67655-94-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) hydrochloric acid, 2.) triethylamine, DCC, HOBt / 1.) dioxane, 30 min, 25 deg C 2.) methylene chloride 2: 1.) TFA, 2.) H2, Pd/C / 1.) room temperature, 30 min 2.) methanol, 24 h View Scheme

Cbz-D-Leu-OMe (73397-22-5) → amastatin (67655-94-1)

Conditions

Yield

Multi-step reaction with 6 steps 1: Diisobutylaluminum hydride / toluene / 0.1 h / -78 °C 2: 1.) NaHSO3 / 1.) 5 deg C, overnight, 2.) ethyl acetate, water, room temp., 4 h 3: 90 percent / concentrated HCl / dioxane / 12 h / Heating 4: 73 percent / triethylamine / H2O; dioxane / 25 °C 5: 1.) hydrochloric acid, 2.) triethylamine, DCC, HOBt / 1.) dioxane, 30 min, 25 deg C 2.) methylene chloride 6: 1.) TFA, 2.) H2, Pd/C / 1.) room temperature, 30 min 2.) methanol, 24 h View Scheme

Upstream product

• 73397-34-9 (2S,3R)-<3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoyl>-L-valyl-L-valyl-aspartic Acid Dibenzyl Ester 
• 13734-41-3 t-Boc-L-valine 
• 70853-19-9 Boc-Val-Asp(OBzl)-OBzl 
• 70853-22-4 <(tert-Butyloxy)carbonyl>-L-valyl-L-valyl-L-aspartic Acid Dibenzyl Ester 
• 70853-20-2 Val-Asp(OBzl)-OBzl 
• 70853-23-5 Val-Val-Asp(OBzl)-OBzl 
• 70853-26-8 (R)-4-methyl-1-oxopentane-2-benzylcarbamate 
• 63219-62-5 [(S)-1-((S)-Cyano-hydroxy-methyl)-3-methyl-butyl]-carbamic acid benzyl ester 
• 62023-30-7 (2RS,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid 
• 73397-25-8 (2RS,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid 
• 73397-22-5 Cbz-D-Leu-OMe 

Relevant articles and documents

Synthesis and structure-activity relationships of amastatin analogues, inhibitors of aminopeptidase A

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