Vancosamine / Saccharosamine CAS No. 36480-36-1

Product Description

Vancosamine is an unusual deoxygenated amino sugar that constitutes a critical, stereospecific building block of the glycopeptide antibiotic vancomycin and several related drugs. Missing hydroxyl groups at C-2 and C-6 and bearing a methylated C-3 amino substituent in the L-configuration, vancosamine is biosynthesized from TDP-glucose through a cascade of tailoring enzymes that effect dehydration, transamination and C-methylation. Its 3-amino group is essential for high-affinity recognition of the D-Ala-D-Ala terminus of bacterial peptidoglycan precursors, thereby conferring vancomycin’s potent activity against MRSA and other Gram-positive pathogens. Although the term “saccharosamine” is occasionally encountered as a synonym, it properly denotes the D-arabino diastereomer found in saccharomicin; thus L-vancosamine and D-saccharosamine are stereoisomeric 3-amino-2,3,6-trideoxyhexoses that share a common biosynthetic origin yet populate distinct natural-product scaffolds.

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Product Use & Characteristics

1. Identity & Synonyms

• Common Name: Vancosamine

• Synonym: Saccharosamine

• IUPAC Name: (3S,4S,5S)-3-amino-4,5-dihydroxy-3-methylhexanal

• Molecular Formula: C₇H₁₅NO₃

• Molecular Weight: 161.2 g/mol

2. Structural & Chemical Properties

• Class: Rare 3-amino-2,6-dideoxy sugar (deoxysugar)

• Key Features:

  • Amino group at C3

  • Missing hydroxyls at C2 and C6 (2,6-dideoxy)

  • Methyl substituent at C3

  • Stereochemistry: L-configured in natural products (e.g., vancomycin)

3. Uses & Applications

• Antibiotic Component:

  • Essential building block in vancomycin (last-resort glycopeptide antibiotic for MRSA/VRE).

  • Critical for saccharomicins (heptadecasaccharide antibiotics active against Gram-positive/-negative bacteria).

• Research Tool:

  • Scaffold for antibiotic analog synthesis to combat antimicrobial resistance.

  • Enables structure–activity relationship (SAR) studies via glycosylation modifications.

4. Synthesis Methods

• Hectogram-Scale Synthesis:

  • Route: 8-step process from mannose (abundant feedstock).

  • Techniques: 3 batch + 5 continuous-flow steps, no chromatography required.

  • Yield: Streamlined, scalable, and environmentally sustainable.

  • Reference: Chin. J. Org. Chem. (2025).

• Glycosylation Stereocontrol:

  • Mechanism: Promoter-dependent SN2-like reactions (α/β-selectivity).

  • Key Finding: DFT-guided selection of Lewis acids (e.g., BF₃·OEt₂) directs α- or β-linkages.

  • Reference: Org. Lett. (2023).

5. Biosynthesis (Natural Context)

• Pathway: Derived from TDP-glucose via enzymes:

  1. Dehydration (C4/C6 modifications).

  2. C3-transamination.

  3. C3-methylation.

• Genes: antB1–antB7 (in Pseudonocardia antarctica) encode vancosamine production for antarmycins (deep-sea macrodiolide antibiotics).

6. Related Compounds

• D-Saccharosamine: Diastereomer (D-arabino configuration) found in saccharomicin B.

• 4-Epi-L-Vancosamine: C4-epimer used in synthetic fragments of saccharomicins.

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