Orthogonally protected, carboxy-activated L-homoisoserine, 2-methyl-L-homoisoserine, and homoisocysteine derivatives. New building blocks for peptide and depsipeptide modification

Klaus Burger; Gabor Radics; Lothar Hennig; Christoph Böttcher; Jan Spengler; Fernando Albericio

doi:10.1007/s00706-005-0291-1

Orthogonally protected, carboxy-activated L-homoisoserine, 2-methyl-L-homoisoserine, and homoisocysteine derivatives. New building blocks for peptide and depsipeptide modification

Klaus Burger
, Gabor Radics
, Lothar Hennig
, Christoph Böttcher
, Jan Spengler
, Fernando Albericio

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

4 Scopus citations

Abstract

Starting from L-malic, L-citramalic, and rac. thiomalic acids routes to L-homoisoserine, 2-methyl-L-homoisoserine and rac. homoisocysteine have been developed. The new orthogonally protected and carboxy-activated building blocks are GABA as well as α-hydroxy and α-mercapto acid derivatives, suitable for the construction of peptide and depsipeptide surrogates.

Original language	English
Pages (from-to)	763-776
Number of pages	14
Journal	Monatshefte fur Chemie
Volume	136
Issue number	5
DOIs	https://doi.org/10.1007/s00706-005-0291-1
State	Published - May 2005
Externally published	Yes

Keywords

α-Hydroxy acids
α-Mercapto acids
γ-Amino acids
Arndt-Eistert reaction
Azapeptides
Citramalic acid
Curtius rearrangement
Depsipeptide modification
Hexafluoroacetone
Malic acid
Peptide modification
Thiomalic acid
Wolff rearrangement

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10.1007/s00706-005-0291-1

Cite this

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title = "Orthogonally protected, carboxy-activated L-homoisoserine, 2-methyl-L-homoisoserine, and homoisocysteine derivatives. New building blocks for peptide and depsipeptide modification",

abstract = "Starting from L-malic, L-citramalic, and rac. thiomalic acids routes to L-homoisoserine, 2-methyl-L-homoisoserine and rac. homoisocysteine have been developed. The new orthogonally protected and carboxy-activated building blocks are GABA as well as α-hydroxy and α-mercapto acid derivatives, suitable for the construction of peptide and depsipeptide surrogates.",

keywords = "α-Hydroxy acids, α-Mercapto acids, γ-Amino acids, Arndt-Eistert reaction, Azapeptides, Citramalic acid, Curtius rearrangement, Depsipeptide modification, Hexafluoroacetone, Malic acid, Peptide modification, Thiomalic acid, Wolff rearrangement",

author = "Klaus Burger and Gabor Radics and Lothar Hennig and Christoph B{\"o}ttcher and Jan Spengler and Fernando Albericio",

year = "2005",

month = may,

doi = "10.1007/s00706-005-0291-1",

language = "Ingl{\'e}s",

volume = "136",

pages = "763--776",

journal = "Monatshefte fur Chemie",

issn = "0026-9247",

publisher = "Springer",

number = "5",

}

TY - JOUR

T1 - Orthogonally protected, carboxy-activated L-homoisoserine, 2-methyl-L-homoisoserine, and homoisocysteine derivatives. New building blocks for peptide and depsipeptide modification

AU - Burger, Klaus

AU - Radics, Gabor

AU - Hennig, Lothar

AU - Böttcher, Christoph

AU - Spengler, Jan

AU - Albericio, Fernando

PY - 2005/5

Y1 - 2005/5

N2 - Starting from L-malic, L-citramalic, and rac. thiomalic acids routes to L-homoisoserine, 2-methyl-L-homoisoserine and rac. homoisocysteine have been developed. The new orthogonally protected and carboxy-activated building blocks are GABA as well as α-hydroxy and α-mercapto acid derivatives, suitable for the construction of peptide and depsipeptide surrogates.

AB - Starting from L-malic, L-citramalic, and rac. thiomalic acids routes to L-homoisoserine, 2-methyl-L-homoisoserine and rac. homoisocysteine have been developed. The new orthogonally protected and carboxy-activated building blocks are GABA as well as α-hydroxy and α-mercapto acid derivatives, suitable for the construction of peptide and depsipeptide surrogates.

KW - α-Hydroxy acids

KW - α-Mercapto acids

KW - γ-Amino acids

KW - Arndt-Eistert reaction

KW - Azapeptides

KW - Citramalic acid

KW - Curtius rearrangement

KW - Depsipeptide modification

KW - Hexafluoroacetone

KW - Malic acid

KW - Peptide modification

KW - Thiomalic acid

KW - Wolff rearrangement

UR - https://www.scopus.com/pages/publications/18544382656

U2 - 10.1007/s00706-005-0291-1

DO - 10.1007/s00706-005-0291-1

M3 - Artículo

AN - SCOPUS:18544382656

SN - 0026-9247

VL - 136

SP - 763

EP - 776

JO - Monatshefte fur Chemie

JF - Monatshefte fur Chemie

IS - 5

ER -

Orthogonally protected, carboxy-activated L-homoisoserine, 2-methyl-L-homoisoserine, and homoisocysteine derivatives. New building blocks for peptide and depsipeptide modification

Abstract

Keywords

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