N-substituted 2-amino-4-pentenoic acids for amino acid protection and resolution

Michiel Lodder; Bixun Wang; Sidney M. Hecht

doi:10.1016/S0040-4020(00)00826-7

N-substituted 2-amino-4-pentenoic acids for amino acid protection and resolution

Michiel Lodder, Bixun Wang, Sidney M. Hecht

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

6 Scopus citations

Abstract

N-Substituted 2-amino-4-pentenoic acid derivatives employed for the protection of racemic amino acids were shown to be capable of permitting the chromatographic separation of R and S isomers. When N(α) was disubstituted with benzyl and phenylfluorenyl groups, the racemic amino acids could be separated with facility on open silica gel columns. Further, the optically pure N-protected amino acids so derived could be used for the preparation of misacylated suppressor transfer RNAs. (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	9421-9429
Number of pages	9
Journal	Tetrahedron
Volume	56
Issue number	48
DOIs	https://doi.org/10.1016/S0040-4020(00)00826-7
State	Published - Nov 24 2000
Externally published	Yes

Keywords

Amino acids and derivatives
Optical properties
Protecting groups
Resolution

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(00)00826-7

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title = "N-substituted 2-amino-4-pentenoic acids for amino acid protection and resolution",

abstract = "N-Substituted 2-amino-4-pentenoic acid derivatives employed for the protection of racemic amino acids were shown to be capable of permitting the chromatographic separation of R and S isomers. When N(α) was disubstituted with benzyl and phenylfluorenyl groups, the racemic amino acids could be separated with facility on open silica gel columns. Further, the optically pure N-protected amino acids so derived could be used for the preparation of misacylated suppressor transfer RNAs. (C) 2000 Elsevier Science Ltd.",

keywords = "Amino acids and derivatives, Optical properties, Protecting groups, Resolution",

author = "Michiel Lodder and Bixun Wang and Hecht, {Sidney M.}",

note = "Funding Information: This work was supported by NIH Research Grant CA77359 awarded by the National Cancer Institute. ",

year = "2000",

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doi = "10.1016/S0040-4020(00)00826-7",

language = "English (US)",

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pages = "9421--9429",

journal = "Tetrahedron",

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T1 - N-substituted 2-amino-4-pentenoic acids for amino acid protection and resolution

AU - Lodder, Michiel

AU - Wang, Bixun

AU - Hecht, Sidney M.

N1 - Funding Information: This work was supported by NIH Research Grant CA77359 awarded by the National Cancer Institute.

PY - 2000/11/24

Y1 - 2000/11/24

N2 - N-Substituted 2-amino-4-pentenoic acid derivatives employed for the protection of racemic amino acids were shown to be capable of permitting the chromatographic separation of R and S isomers. When N(α) was disubstituted with benzyl and phenylfluorenyl groups, the racemic amino acids could be separated with facility on open silica gel columns. Further, the optically pure N-protected amino acids so derived could be used for the preparation of misacylated suppressor transfer RNAs. (C) 2000 Elsevier Science Ltd.

AB - N-Substituted 2-amino-4-pentenoic acid derivatives employed for the protection of racemic amino acids were shown to be capable of permitting the chromatographic separation of R and S isomers. When N(α) was disubstituted with benzyl and phenylfluorenyl groups, the racemic amino acids could be separated with facility on open silica gel columns. Further, the optically pure N-protected amino acids so derived could be used for the preparation of misacylated suppressor transfer RNAs. (C) 2000 Elsevier Science Ltd.

KW - Amino acids and derivatives

KW - Optical properties

KW - Protecting groups

KW - Resolution

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U2 - 10.1016/S0040-4020(00)00826-7

DO - 10.1016/S0040-4020(00)00826-7

M3 - Article

AN - SCOPUS:0034711441

SN - 0040-4020

VL - 56

SP - 9421

EP - 9429

JO - Tetrahedron

JF - Tetrahedron

IS - 48

ER -

N-substituted 2-amino-4-pentenoic acids for amino acid protection and resolution

Abstract

Keywords

ASJC Scopus subject areas

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