A chiron approach towards the synthesis of 3-hydroxy lysine and its derivatives

K. S.Ajish Kumar

doi:10.1016/j.bmc.2013.02.013

A chiron approach towards the synthesis of 3-hydroxy lysine and its derivatives

K. S.Ajish Kumar

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

A general and efficient route towards the synthesis of three derivatives of structurally and functionally important amino acid, lysine is reported. Chemoselective reduction of aldehydic functionality in C-3-azido conjugated aldehyde 4, under Luche condition, is the key step in the synthetic sequence. The lysine derivative, (2S,3R)-2,6-diazido-3-hydroxy-hex-4-ene-oic acid 9 could be used to prepare switch peptide using Staudinger reaction, while the unprotected (2S,3R)-2,6-diamino-3-hydroxy-hexanoic acid hydrochloride 10 is a proven reaction intermediate towards the synthesis of natural product (-)-Balanol.

Original language	English
Pages (from-to)	3609-3613
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry
Volume	21
Issue number	12
DOIs	https://doi.org/10.1016/j.bmc.2013.02.013
State	Published - 15 Jun 2013
Externally published	Yes

Keywords

Native chemical ligation
Nonproteinogenic amino acids

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2013.02.013

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abstract = "A general and efficient route towards the synthesis of three derivatives of structurally and functionally important amino acid, lysine is reported. Chemoselective reduction of aldehydic functionality in C-3-azido conjugated aldehyde 4, under Luche condition, is the key step in the synthetic sequence. The lysine derivative, (2S,3R)-2,6-diazido-3-hydroxy-hex-4-ene-oic acid 9 could be used to prepare switch peptide using Staudinger reaction, while the unprotected (2S,3R)-2,6-diamino-3-hydroxy-hexanoic acid hydrochloride 10 is a proven reaction intermediate towards the synthesis of natural product (-)-Balanol.",

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AB - A general and efficient route towards the synthesis of three derivatives of structurally and functionally important amino acid, lysine is reported. Chemoselective reduction of aldehydic functionality in C-3-azido conjugated aldehyde 4, under Luche condition, is the key step in the synthetic sequence. The lysine derivative, (2S,3R)-2,6-diazido-3-hydroxy-hex-4-ene-oic acid 9 could be used to prepare switch peptide using Staudinger reaction, while the unprotected (2S,3R)-2,6-diamino-3-hydroxy-hexanoic acid hydrochloride 10 is a proven reaction intermediate towards the synthesis of natural product (-)-Balanol.

KW - Native chemical ligation

KW - Nonproteinogenic amino acids

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JO - Bioorganic and Medicinal Chemistry

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ER -

A chiron approach towards the synthesis of 3-hydroxy lysine and its derivatives

Abstract

Keywords

ASJC Scopus subject areas

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