C5 Organic Synthesis · D-erythro and L-erythro isomers · –NH₂ at C3

3-Amino-3-deoxy-dihydrosphingosines

Dihydrosphingosine derivatives in which the C3 hydroxyl is replaced by an amino group. The D-erythro and L-erythro isomers show distinct biological activity, and the amino group enables stronger protein kinase C inhibition — relevant to cell signalling and apoptosis research.

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Evidence: Synthetic capability · characterisation on request
Stage: Synthesis to order
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Structures of D-erythro-sphinganine analogues — 3-amino-3-deoxy-dihydrosphingosine isomers — D-erythro-sphinganine analogues — 3-amino-3-deoxy-dihydrosphingosine isomers

Scientific summary

These are dihydrosphingosine derivatives in which the hydroxyl group at C3 is replaced by an amino group. The D-erythro and L-erythro isomers show distinct biological activity, and the amino group enables stronger protein kinase C inhibition than the parent alcohol.

Where the substitution matters

Swapping –OH for –NH₂ changes both the hydrogen-bonding pattern and the charge state at physiological pH. That is what makes these compounds useful as molecular probes: the difference in activity between the isomer pair is interpretable rather than incidental.

Applications

Molecular probes for sphingolipid biology
Protein kinase C inhibition studies
Apoptosis research
Sphingolipid metabolism research

Specification

Compound type	Amino-substituted dihydrosphingosine derivatives
Stereochemistry	D-erythro · L-erythro
Research group	Department of Organic Chemistry, Faculty of Science, UPJŠ
Evidence status	Synthesis capability; characterisation data on request
Supply	Synthesised to order
Engagement	Custom synthesis · pilot
Indicative price	Price on request, by quantity and application

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