6379-56-2

Basic information

• Product Name: hygromycin A
• Synonyms: hygromycin A;5-Deoxy-5-[[(2E)-3-[4-[(6-deoxy-β-D-arabino-5-hexosulofuranosyl)oxy]-3-hydroxyphenyl]-2-methyl-1-oxo-2-propenyl]amino]-1-O,2-O-methylene-D-neo-inositol;Antibiotic WS-1627B;Homomycin;Hygromycin
• CAS NO: 6379-56-2
• Molecular Formula: C₂₃H₂₉NO₁₂
• Molecular Weight: 511.477
• Mol File: 6379-56-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 105-109°; mp 110-112° (dec) (Chida)
• Appearance: /
• Refractive Index: 1.667
• PKA: 8.9(at 25℃)
• CAS DataBase Reference: hygromycin A(CAS DataBase Reference)
• NIST Chemistry Reference: hygromycin A(6379-56-2)
• EPA Substance Registry System: hygromycin A(6379-56-2)

Safety Data

• Hazardous Substances Data: 6379-56-2(Hazardous Substances Data)

Usage

Description

Hygromycin A is a natural product derived from Streptomyces species, specifically produced by Streptomyces hygroscopicus. It is a white powder with weakly acidic properties and is freely soluble in water and alcohol. Hygromycin A has gained attention for its selective antibacterial activity against the bacteria responsible for Lyme disease.

Uses

Used in Medicine:
Hygromycin A is used as a broad-spectrum antibiotic for treating various bacterial infections. Its unique property of selectively targeting the bacteria that cause Lyme disease without disrupting the overall microbiome makes it a valuable addition to the arsenal of antibiotics available for medical use.
Used in Lyme Disease Treatment:
Hygromycin A is used as an antibiotic specifically for treating Lyme disease. It has been shown to effectively treat the disease in mice without causing significant disruption to the microbiome, which is a common concern with the use of broad-spectrum antibiotics. This selective action against the Lyme disease-causing bacteria makes it a promising candidate for further research and potential clinical applications in human patients.

InChI:InChI=1/C23H29NO12/c1-8(22(32)24-13-14(27)16(29)21-20(15(13)28)33-7-34-21)5-10-3-4-12(11(26)6-10)35-23-18(31)17(30)19(36-23)9(2)25/h3-6,13-21,23,26-31H,7H2,1-2H3,(H,24,32)/b8-5+/t13-,14+,15-,16-,17-,18-,19+,20+,21-,23+/m0/s1

Upstream product

• 127213-11-0 hygromycin A ethylene acetal 
• 122777-43-9 Acetic acid (2S,3S,4S,5S)-4-acetoxy-5-{2-acetoxy-4-[(E)-2-((3aS,4R,5S,6S,7R,7aS)-4,6,7-triacetoxy-hexahydro-benzo[1,3]dioxol-5-ylcarbamoyl)-propenyl]-phenoxy}-2-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-yl ester 
• 122777-35-9 2-acetoxy-4-<(E)-2-carboxy-1-propen-1-yl>phenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal 
• 127213-09-6 2-acetoxy-4-methylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal 
• 122777-42-8 2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal 
• 127213-10-9 2-acetoxy-4-<(E)-2-(ethoxycarbonyl)-1-propen-1-yl>phenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal 
• 118068-47-6 2-acetoxy-4-methylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside 
• 33164-03-3 methyl 2,3-di-O-benzyl-α-D-altropyranoside 
• 118068-40-9 (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol 
• 118068-41-0 2,3-di-O-benzyl-6-deoxy-D-arabino-5-hexulofuranose 
• 118068-39-6 methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside 
• 99212-27-8 methyl 4,6-O-benzylidene-2,3-di-O-benzyl-α-D-altropyranoside 
• 118068-43-2 4-((3S,4S,5S)-5-Acetyl-3,4-bis-benzyloxy-tetrahydro-furan-2-yloxy)-3-benzyloxy-benzaldehyde 
• 118068-45-4 2-hydroxy-4-methylphenyl 6'-deoxy-β-D-arabino-5'-hexulofuranoside 

Downstream Products

• 66740-54-3 Hygromycin-hexaacetat 

Relevant articles and documents

Chiral pool based efficient synthesis of the aminocyclitol core and furanoside of (-)- hygromycin A: Formal total synthesis of (-)-hygromycin A

A chiral pool based synthetic strategy that leads from the readily available and inexpensive C2-symmetric tartaric acids to the chiral O-isopropylidenebenzooxazolei- a convenient precursor to the aminocyclitol core of hygromycin A as well as the chiral γ-disilyloxybutyrolactone-a pivotal intermediate to approach to the furanoside of hygromycin A.

Total Synthesis of Antibiotic Hygromycin A

The first total synthesis of the antibiotic (-)-hygromycin A (1) has been achieved by a coupling reaction of the sugar moiety (2) and the cyclitol moiety (3).Both components were synthesized in homochiral forms starting from D-glucose.This synthesis fully