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Synfacts 2022; 18(04): 0454
DOI: 10.1055/s-0041-1737549
Peptide Chemistry

Solid-Phase Synthesis of α-Amino Alkyl or Aryl Phosphonopeptide Derivatives

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
Rinnová M, Nefzi A, Houghten RA. * Torrey Pines Institute for Molecular Studies, San Diego, USA
An Expedient Method for the Solid-Phase Synthesis of α-Aminoalkyl Phosphonopeptides.

Tetrahedron Lett. 2002;
43: 4103-4106
DOI: 10.1016/S0040-4039(02)00695-0
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Key words

phosphonopeptides - solid-phase synthesis - aldehyde dimethylphosphite

Significance

Amino phosphonopeptides are highly significant molecules in biological systems as potent antimicrobial agents and as inhibitors of various enzymes. In 2002, Houghten and co-workers developed a solid-phase synthesis of α-aminoalkyl phosphonopeptides by using an aldehyde dimethylphosphite in the presence of the Lewis acid BF3·Et2O.


 

Comment

The developed method is one of the simplest and practically most viable methods for the generation of series of α-aminoalkyl or aryl phosphonopeptide derivatives in high yields with moderate stereoselectivity. The method can be used for the synthesis of libraries of peptide or nonpeptide phosphonates.


 

 

Publication History

Article published online:
18 March 2022

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