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A practical route to long-chain non-natural α,ω-diamino acids

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Abstract

An efficient method for the synthesis of long-chain α,ω-diamino acids, starting from natural α-amino acids, has been developed. The long-chain skeleton has been generated through condensation between a protected aldehyde, derived from l-aspartic acid, and an ylide obtained from an ω-hydroxy-alkyl phosphonium salt. After conversion of the ω-hydroxy group into an amine, catalytic hydrogenation produced the N,N′-protected α,ω-diamino acid. The present route to α,ω-diamino acids allows the modulation of the chain length depending on the length of the ylide used for the Wittig olefination reaction.

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Fig. 1
Scheme 1

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Abbreviations

TEA:

Triethylamine

LiHMDS:

Lithium hexamethyldisilazide

TsCl:

p-Toluenesulfonyl chloride

DMAP:

4-Dimethylamino pyridine

DIPEA:

N,N-Diisopropylethylamine

TBAI:

Tetrabutylammonium iodide

PPh3 :

Triphenylphosphine

Boc2O:

Di-tert-butyl dicarbonate

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Acknowledgments

We gratefully acknowledge the University of Milan for financial support.

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Authors and Affiliations

  1. Dipartimento di Biotecnologie Mediche e Medicina Traslazionale, Università di Milano, Via Saldini 50, 20133, Milano, Italy

    Giuseppina Brasile, Federica Compostella & Fiamma Ronchetti

  2. Dipartimento di Biotecnologie Mediche e Medicina Traslazionale, Università di Milano, Via Fratelli Cervi 93, 20190, Segrate (Milano), Italy

    Laura Mauri & Sandro Sonnino

Authors
  1. Giuseppina Brasile
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  2. Laura Mauri
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  3. Sandro Sonnino
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  4. Federica Compostella
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  5. Fiamma Ronchetti
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Corresponding author

Correspondence to Federica Compostella.

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Brasile, G., Mauri, L., Sonnino, S. et al. A practical route to long-chain non-natural α,ω-diamino acids. Amino Acids 44, 435–441 (2013). https://doi.org/10.1007/s00726-012-1349-0

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  • DOI: https://doi.org/10.1007/s00726-012-1349-0

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