527-06-0

Basic information

• Product Name: PERSEITOL FROM AVOCARDO
• Synonyms: PERSEITOL FROM AVOCARDO;D-glycero-D-galacto-heptitol;Perseitol from Perseau americana (avocado);α-Mannoheptitol, D-Glycero-D-galactoheptitol;Einecs 208-406-1;Nsc 1976;Peracitol;Perseitol (D)
• CAS NO: 527-06-0
• Molecular Formula: C7H16O7
• Molecular Weight: 212.196
• EINECS: 208-406-1
• Mol File: 527-06-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 188°C
• Boiling Point: 272.03°C (rough estimate)
• Flash Point: 319°C
• Appearance: /
• Density: 1.2974 (rough estimate)
• Vapor Pressure: 3.03E-18mmHg at 25°C
• Refractive Index: 1.4455 (estimate)
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.13±0.20(Predicted)
• Water Solubility: 64.60g/L(18 oC)
• CAS DataBase Reference: PERSEITOL FROM AVOCARDO(CAS DataBase Reference)
• NIST Chemistry Reference: PERSEITOL FROM AVOCARDO(527-06-0)
• EPA Substance Registry System: PERSEITOL FROM AVOCARDO(527-06-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 527-06-0(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white solid

Definition

ChEBI: A heptitol that is heptane-1,2,3,4,5,6,7-heptol that has R-configuration at positions 2, 3, 4 and 5, and S-configuration at position 6.

Enzyme inhibitor

This seven-carbon sugar polyol (FW = 212,20 g/mol; CAS 527-06-0), also known as D-glycero-D-galacto-heptitol and a-mannoheptitol, from the avocado (Persea americana) and leaves of Scurrula fusca. Perseitol inhibits EIImtl, the membrane-bound mannitol-specific enzyme II (EIIMtl) of the phosphoenolpyruvate-dependent phosphotransferase of Escherichia coli.

InChI:InChI=1/C7H16O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3-14H,1-2H2/t3-,4+,5-,6-,7?/m1/s1

Upstream product

• 189571-81-1 1,2:3,4-di-O-isopropylidene-D/L-glycero-α-D-galacto-1,5-pyranose 
• 15397-08-7 D-glycero-D-galacto-heptono-1,4-lactone 
• 1231714-26-3 7-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-glycero-D-galacto-heptitol 
• 3019-74-7 sedoheptulose 
• 1187860-93-0 4-O-benzyl-5,7-O-benzylidene-3,6-O-methylene-D-glycero-D-galacto-heptitol 
• 105592-36-7 benzyl (E)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside 
• 108182-76-9 benzyl (E)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enodialdo-1,4-furanoside 
• 102919-04-0 benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside 
• 74912-02-0 1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose 
• 35810-57-2 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-D-galacto-hept-6-enopyranose 
• 4933-77-1 (3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde 
• 105592-29-8 (1R,2S)-1-((3aR,4S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propane-1,2,3-triol 
• 3615-44-9 D-mannoheptulose 

Downstream Products

• 6893-84-1 D-glycero-D-gluco-heptitol hepta acetate 
• 7510-98-7 L-(1R)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-xylitol 
• 3624-30-4 L-gulo-[2]heptosulose-bis-phenylhydrazone 
• 3624-30-4 L-gluco-[2]heptosulose-bis-phenylhydrazone 
• 591-49-1 1-methylcyclohex-1-ene 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 6893-84-1 Acetic acid (1R,2R,3S)-2,3,4-triacetoxy-1-((1S,2S)-1,2,3-triacetoxy-propyl)-butyl ester 
• 6893-84-1 meso-glycero-ido-heptitol acetate 
• 6893-84-1 perseitol heptaacetate 
• 6893-84-1 Hepta-O-acetyl-L-glycero-D-glucoheptit 
• 4141-44-0 O¹,O³;O⁵,O⁷-((Ξ,Ξ)-dibenzylidene)-L-glycero-L-galacto-heptitol 
• 5345-81-3 O³,O⁵-((s)-benzylidene)-D-glycero-D-gulo-heptitol 
• 6893-84-1 1,2,3,4,5,6,7-heptaacetoxy-heptane 

Relevant articles and documents

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Organocatalytic Synthesis of Higher-Carbon Sugars: Efficient Protocol for the Synthesis of Natural Sedoheptulose and d-Glycero-l-galacto-oct-2-ulose

Herein we report a short and efficient protocol for the synthesis of naturally occurring higher-carbon sugars—sedoheptulose (d-altro-hept-2-ulose) and d-glycero-l-galacto-oct-2-ulose—from readily available sugar aldehydes and dihydroxyacetone (DHA). The key step includes a diastereoselective organocatalytic syn-selective aldol reaction of DHA with d-erythrose and d-xylose, respectively. The methodology presented can be expanded to the synthesis of various higher sugars by means of syn-selective carbon–carbon-bond-forming aldol reactions promoted by primary-based organocatalysts. For example, this methodology provided useful access to d-glycero-d-galacto-oct-2-ulose and 1-deoxy-d-glycero-d-galacto-oct-2-ulose from d-arabinose in high yield (85 and 74 %, respectively) and high stereoselectivity (99:1).

Four orders of magnitude rate increase in artificial enzyme-catalyzed aryl glycoside hydrolysis

(6A6DR)-6A,6D-Di-C-cyano- β-cyclodextrin (1) and 6A,6D-di-C-cyano-α- cyclodextrin (2) were synthesized and shown to catalyze hydrolysis of aryl glycosides into glucose and phenol with a reaction following Michaelis-Menten kinetics. At pH 8.0 and 59 °C hydrolysis of 4-nitrophenyl α-glucopyranoside was catalyzed by 1 with KM = 10.5 ± 1.5 mM, kcat = 1.42(±0.09) × 10-4 s -1 and kcatk/uncat = 7922, Catalysis was observed with a concentration of 1 as low as 10 μM. Hydrolysis of the other aryl glycosides containing stereochemical variation in the sugar-moiety and 4-nitro-, 2-nitro-, 2-aldehydo-, and 2,4-dinitro- were also catalyzed by 1 and 2 with kcat/kuncat ranging from 4 to 7100. Hydrolysis of a phenyl β-D-glucoside or the thioglycoside tolylthio β-D-glucoside was also catalyzed. From a series of prepared analogues of 1 it was found that the catalysis was associated with the hydroxyl groups α to the nitril groups. The monocyanohydrin 6-C-cyano-β-cyclodextrin (3) was also found to catalyze the hydrolysis of 4-nitrophenyl β-glucopyranoside with k Cat/kuncat = 1356. It was proposed that the cyclodextrin cyanohydrins 1-3 catalyze the hydrolysis by general acid catalysis on the bound substrate.