76224-57-2

Basic information

• Product Name: Avenic acid
• Synonyms: Avenic acid;Avenic acid A;N-[(S)-3-Carboxy-3-[[(S)-3-carboxy-3-hydroxypropyl]amino]propyl]-L-homoserine
• CAS NO: 76224-57-2
• Molecular Formula: C₁₂H₂₂N₂O₈
• Molecular Weight: 322.31168
• Mol File: 76224-57-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Avenic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Avenic acid(76224-57-2)
• EPA Substance Registry System: Avenic acid(76224-57-2)

Safety Data

• Hazardous Substances Data: 76224-57-2(Hazardous Substances Data)

Upstream product

• 79848-46-7 (S)-2-Benzyloxycarbonylamino-4-((S)-2-oxo-tetrahydro-furan-3-ylamino)-butyric acid tert-butyl ester 
• 77856-44-1 L-tert-butoxycarbonyl-N<3-O-tetrahydropyranyl-3-carboxybenzylpropyl>homoserine aldehyde benzyl ester 
• 79438-09-8 (S)-2-{[(S)-3-Benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-4-((S)-2-oxo-tetrahydro-furan-3-ylamino)-butyric acid benzyl ester 
• 79438-11-2 (S)-2-((S)-3-Carboxy-3-hydroxy-propylamino)-4-((S)-2-oxo-tetrahydro-furan-3-ylamino)-butyric acid; compound with trifluoro-acetic acid 
• 79848-47-8 (S)-2-((S)-3-Acetoxy-3-ethoxycarbonyl-propylamino)-4-((S)-2-oxo-tetrahydro-furan-3-ylamino)-butyric acid tert-butyl ester 

Downstream Products

• 1927-25-9 DL-Homoserine 
• 617-48-1 malic acid 
• 617-45-8 aspartic Acid 

Relevant articles and documents

SYNTHESIS OF (+)-AVENIC ACID A

Avenic acid A (2), the metal chelator excreted from oat root and the factor which is considered to be directly involved in the uptake and transport of iron and other elements, has been synthesized efficiently from L-Nhomoserine

A Unified Approach to Phytosiderophore Natural Products

This work reports on the concise total synthesis of eight natural products of the mugineic acid and avenic acid families (phytosiderophores). An innovative ?east-to-west“ assembly of the trimeric products resulted in a high degree of divergence enabling the formation of the final products in just 10 or 11 steps each with a minimum of overall synthetic effort. Chiral pool starting materials (l-malic acid, threonines) were employed for the outer building blocks while the middle building blocks were accessed by diastereo- and enantioselective methods. A highlight of this work consists in the straightforward preparation of epimeric hydroxyazetidine amino acids, useful building blocks on their own, enabling the first synthesis of 3’’-hydroxymugineic acid and 3’’-hydroxy-2’-deoxymugineic acid.

SYNTHESIS OF AVENIC ACID A AND 2'-DEOXYMUGIENIC ACID, AMINO ACIDS POSSESSING AN IRON CHELATING ACTIVITY

Avenic acid A (1), an amino acid derivative possessing an iron chelating activity and excreted from the root of Avena sativa L. was synthesized in optically active form by successive reductive coupling of protected L-aspartic β-semialdehyde and L-malic semialdehyde with L-homoserine lactone. 2'-Deoxymugineic acid (2), a related substance was also synthesized by the same method by which the stereostructure of this amino acid derivative was proved to be 2(S), 3'(S),3''(S)-N--azetidine-2-carboxylic acid.