69086-72-2

Basic information

• Product Name: (+)-Lycoperdic acid
• Synonyms: (+)-Lycoperdic acid;(2S)-2-Amino-3-[(2S)-2-carboxy-5-oxotetrahydrofuran-2-yl]propionic acid;(2S,αS)-Tetrahydro-α-amino-2-carboxy-5-oxo-2-furanpropionic acid;Lycoperdic acid
• CAS NO: 69086-72-2
• Molecular Formula: C8H11NO6
• Molecular Weight: 217.17604
• Mol File: 69086-72-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-Lycoperdic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Lycoperdic acid(69086-72-2)
• EPA Substance Registry System: (+)-Lycoperdic acid(69086-72-2)

Safety Data

• Hazardous Substances Data: 69086-72-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Lycoperdic acid is used as an antimicrobial agent for its ability to inhibit the growth of various microorganisms, making it a potential candidate for the development of new antibiotics and antifungal treatments.
Used in Food Industry:
(+)-Lycoperdic acid is used as a natural preservative for its antimicrobial properties, helping to extend the shelf life of food products and maintain their quality.
Used in Cosmetics Industry:
(+)-Lycoperdic acid is used as an active ingredient in cosmetic products for its antimicrobial properties, which can help prevent the growth of bacteria and fungi on the skin, promoting a healthier and cleaner complexion.
Used in Agriculture:
(+)-Lycoperdic acid is used as a biopesticide for its antimicrobial properties, helping to protect crops from various diseases and pests, thereby increasing crop yield and quality.

Upstream product

• 856433-16-4 (2S,4S)-4-(tert-butoxycarbonyl)amino-2-[2-(ethoxycarbonyl)ethyl]-5-oxooxolane-2-carboxylic acid 
• 856433-15-3 (2S,4S)-4-(tert-butoxycarbonyl)amino-2-[2-(ethoxycarbonyl)ethyl]-2-(hydroxymethyl)oxolan-5-one 
• 502698-24-0 benzoic (5S,8S)-2,6-dioxo-1-oxa-7-aza-spiro[4.4]nonane-8-carboxylic anhydride 
• 146554-64-5 methyl (5S,8S)-7-tert-butoxycarbonyl-2,6-dioxo-1-oxa-7-azaspiro<4.4>nonane-8-carboxylate 
• 324535-77-5 ((3aR,4S,6R,6aS)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester 
• 3008-40-0 cyclopentane-1,2-dione 

Relevant articles and documents

Total synthesis of lycoperdic acid and its C4-epimer

Efficient stereodivergent syntheses of (+)-lycoperdic acid (LPA) and 4-epi-LPA have been achieved based on asymmetric hydrogenation (H2, Rh/(R,S)-MeBoPhoz) of racemic enamide as a key step.

Synthesis of both enantiomers of lycoperdic acid, an unusual mushroom-derived amino acid

An efficient synthesis of both enantiomers of lycoperdic acid, a 4-hydroxyglutamic acid derivative from edible mushroom Lycoperdon perlatum, was achieved from a chiral aminoalcohol. The key steps were a stereoselective introduction of a C3 unit into a bicyclic ketone and oxidative cleavage of a cyclic vicinal diol into a dicarboxylic acid. This report provides the first synthesis of (?)-lycoperdic acid.

3-Alkyl-1,2-cyclopentanediones by Negishi cross-coupling of a 3-bromo-1,2-cyclopentanedione silyl enol ether with alkylzinc reagents: An approach to 2-substituted carboxylic acid γ-lactones, homocitric and lycoperdic acids

Negishi cross-coupling of the silyl-protected 3-bromoenol of 1,2-cyclopentanedione with primary and secondary alkylzinc reagents using Pd-catalysts affords 3-alkyl substituted 1,2-cyclopentanediones in good yield. The method was applied to obtain 3-methyl

Diastereoselective synthesis of glutamate-appended oxolane rings: Synthesis of (S)-(+)-lycoperdic acid

(Chemical Equation Presented) The stereocontrolled synthesis of the glutamate-containing natural product (S)-(+)-lycoperdic acid is described. The key transformation in the synthetic route was an efficient diastereoselective annulation of an oxolane ring

Stereoselective syntheses of 4-hydroxy 4-substituted glutamic acids

The 4-hydroxy 4-substituted glutamic acid moiety is a common substructure of biologically important natural products such as monatin [(2S,4S)-2], lycoperdic acid (3), and dysiherbaine (4). To develop methodology for syntheses of these natural products, cycloadditions of nitrone 5 with 2-substituted 2-propen-1-ols 6 and 2-substituted acrylates 8 were investigated. Reactions of nitrone 5 with alcohols 6 in the presence of MgBr2OEt2 gave cycloadducts 7 in a highly stereoselective manner, whereas noncatalyzed reactions of 5 with acrylates 8 afforded adducts 9. Using the former reaction, syntheses of monatin [(2S,4S)-2], monatin derivative 18, and lycoperdic acid (3) were accomplished. The C4-epimer of monatin [(2S,4R)-2)] was also synthesized by employing the latter cycloaddition.

Stereoselective synthesis of (S)-(+)-lycoperdic acid through an endo selective hydroxylation of the chiral bicyclic lactam enolate with MoOPH

Efficient synthesis of (S)-(+)-lycoperdic acid has been achieved by use of the stereoselective hydroxylation of the enolate derived from the bicyclic lactam 3 with the molybdenum oxidizing reagent, MoOPH (MoO5·Py·HMPA, oxodiperoxymolybdenum(pyr

Stereocontrolled synthesis of (+)-lycoperdic acid based on a palladium catalyzed reaction using a serine-derived organozinc reagent

An efficient stereocontrolled synthesis of (+)-lycoperdic acid has been achieved based on palladium catalyzed cross-coupling reaction of (Z)-1-(tert- butyldimethylsiloxy)-3-iodo-6-(p-methoxybenzyl)oxy-2-hexene with the organozinc reagent, prepared from N-Boc-β-iodoalanine methyl ester. (C) 2000 Elsevier Science Ltd.

Asymmetric synthesis of lycoperdic acid

Lycoperdic acid [(2S,5'S)-2-amino-3-(5'-carboxy-2'-oxo-5'- tetrahydrofuranyl)propanoic acid], isolated from the mushroom Lycoperdon perlatum, was synthesized from trans-4-hydroxy-L-proline by a six-step route involving samarium diiodide (SmI2)-mediated formation of the spiro-γ- lactone and ruthenium tetroxide (RuO4) oxidation of the L-proline ring system to the L-pyroglutamic acid moiety. Lycoperdic acid (1) was found to undergo hydrolysis of the γ-lactone ring in 1 N hydrochloric acid at 23°C, giving an equilibrated mixture of 1 and the corresponding hydroxy acid.

FIRST SYNTHESIS OF LYCOPERDIC ACID

Lycoperdic acid, (2S,2'S)-2-amino-3-(2'-carboxy-5'-oxo-2'-tetrahydrofuranyl)propanoic acid, was synthesized from trans-4-hydroxy-L-proline.