Synthesis of (R)-Serine-2-d and Its Conversion to the Broad Spectrum Antibiotic Fludalanine

Paul J. Reider; Robin S. Eichen Conn; Paul Davis; Victor J. Grenda; Arthur J. Zambito; Edward J.J. Grabowski

doi:10.1021/jo00391a029

Synthesis of (R)-Serine-2-d and Its Conversion to the Broad Spectrum Antibiotic Fludalanine

Paul J. Reider, Robin S. Eichen Conn, Paul Davis, Victor J. Grenda, Arthur J. Zambito, Edward J.J. Grabowski

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

43 Scopus citations

Abstract

A novel and practical synthesis of (R)-serine-2-d that is stoichiometric in its use of deuterium is described. Isopropyl (R,S)-2-phenyl-2-oxazoline-4-carboxylate is metalated, deuteriated, resolved, and hydrolyzed to provide the optically pure (>99.8%) unnatural amino acid with >98% isotopic purity. Fluorination of the primary hydroxyl with SF₄ produces (S)-3-fluoroalanine-2-d (Fludalanine).

Original language	English (US)
Pages (from-to)	3326-3334
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	52
Issue number	15
DOIs	https://doi.org/10.1021/jo00391a029
State	Published - Jul 1 1987
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00391a029

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title = "Synthesis of (R)-Serine-2-d and Its Conversion to the Broad Spectrum Antibiotic Fludalanine",

abstract = "A novel and practical synthesis of (R)-serine-2-d that is stoichiometric in its use of deuterium is described. Isopropyl (R,S)-2-phenyl-2-oxazoline-4-carboxylate is metalated, deuteriated, resolved, and hydrolyzed to provide the optically pure (>99.8%) unnatural amino acid with >98% isotopic purity. Fluorination of the primary hydroxyl with SF4 produces (S)-3-fluoroalanine-2-d (Fludalanine).",

author = "Reider, {Paul J.} and {Eichen Conn}, {Robin S.} and Paul Davis and Grenda, {Victor J.} and Zambito, {Arthur J.} and Grabowski, {Edward J.J.}",

year = "1987",

month = jul,

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doi = "10.1021/jo00391a029",

language = "English (US)",

volume = "52",

pages = "3326--3334",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Synthesis of (R)-Serine-2-d and Its Conversion to the Broad Spectrum Antibiotic Fludalanine

AU - Reider, Paul J.

AU - Eichen Conn, Robin S.

AU - Davis, Paul

AU - Grenda, Victor J.

AU - Zambito, Arthur J.

AU - Grabowski, Edward J.J.

PY - 1987/7/1

Y1 - 1987/7/1

N2 - A novel and practical synthesis of (R)-serine-2-d that is stoichiometric in its use of deuterium is described. Isopropyl (R,S)-2-phenyl-2-oxazoline-4-carboxylate is metalated, deuteriated, resolved, and hydrolyzed to provide the optically pure (>99.8%) unnatural amino acid with >98% isotopic purity. Fluorination of the primary hydroxyl with SF4 produces (S)-3-fluoroalanine-2-d (Fludalanine).

AB - A novel and practical synthesis of (R)-serine-2-d that is stoichiometric in its use of deuterium is described. Isopropyl (R,S)-2-phenyl-2-oxazoline-4-carboxylate is metalated, deuteriated, resolved, and hydrolyzed to provide the optically pure (>99.8%) unnatural amino acid with >98% isotopic purity. Fluorination of the primary hydroxyl with SF4 produces (S)-3-fluoroalanine-2-d (Fludalanine).

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VL - 52

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

Synthesis of (R)-Serine-2-d and Its Conversion to the Broad Spectrum Antibiotic Fludalanine

Abstract

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