Enzymes in Organic Chemistry, 11:[1] Hydrolase-Catalyzed Resolution of a- and ß-Hydroxyphosphonates and Synthesis of Chiral, Non-Racemic ß-Aminophosphonic Acids (2024)

Lindner, W., & Hammerschmidt, F. (2003). Enzymes in Organic Chemistry, 11:[1] Hydrolase-Catalyzed Resolution of a- and ß-Hydroxyphosphonates and Synthesis of Chiral, Non-Racemic ß-Aminophosphonic Acids. , 345(12), 1287-1298.

Lindner, Wolfgang ; Hammerschmidt, Friedrich. / Enzymes in Organic Chemistry, 11:[1] Hydrolase-Catalyzed Resolution of a- and ß-Hydroxyphosphonates and Synthesis of Chiral, Non-Racemic ß-Aminophosphonic Acids. in: . 2003 ; Band 345, Nr. 12. S. 1287-1298.

@article{e6892822d88a4e1f9113bf82084a3e68,

title = "Enzymes in Organic Chemistry, 11:[1] Hydrolase-Catalyzed Resolution of a- and {\ss}-Hydroxyphosphonates and Synthesis of Chiral, Non-Racemic {\ss}-Aminophosphonic Acids",

abstract = "The enantioselective acylation of racemic diisopropyl a- and {\ss}-hydroxyphosphonates by hydrolases in t-butyl methyl ether with isopropenyl acetate as acyl donor is limited by the narrow substrate specificity of the enzymes. High enantiomeric excesses (up to 99%) were obtained for the acetates of (S)-diisopropyl 1-hydroxy-(2-thienyl)methyl-, 1-hydroxyethyl- and 1-hydroxyhexylphosphonate and (R)-diisopropyl 2-hydroxypropylphosphonate. The hydrolysis of a variety of {\ss}- chloroacetoxyphosphonates by the lipase from Candida cylindracea and protease subtilisin in a biphasic system gives (S)-{\ss}-hydroxyphosphonates (ee 51-92%) enantioselectively. (S)-2-Phenyl-2-hydroxyethyl- and (S)-3-methyl-2- hydroxybutylphosphonates (ee 96% and 99%, respectively) were transformed into (R)-2-aminophosphonic acids of the same ee.",

author = "Wolfgang Lindner and Friedrich Hammerschmidt",

note = "Zeitschrift: Advanced Synthesis and Catalysis Coden: JPCHF Affiliations: Institut f{\"u}r Organische Chemie, Universit{\"a}t Wien, W{\"a}hringerstra{\ss}e 38, 1090 Wien, Austria; Institut f{\"u}r Analytische Chemie, Universit{\"a}t Wien, W{\"a}hringerstra{\ss}e 38, A-1090 Wien, Austria Adressen: Hammerschmidt, F.; Institut f{\"u}r Organische Chemie; Universit{\"a}t Wien; W{\"a}hringerstra{\ss}e 38 1090 Wien, Austria; email: friedrich.hammerschmidt@univie.ac.at Source-File: ChemieErgScopus.csv Import aus Scopus: 2-s2.0-1642576230 Importdatum: 09.01.2007 14:10:46 22.10.2007: Datenanforderung 1934 (Import Sachbearbeiter)",

year = "2003",

language = "English",

volume = "345",

pages = "1287--1298",

journal = "Advanced Synthesis & Catalysis",

issn = "1615-4150",

publisher = "WILEY-V C H VERLAG GMBH",

number = "12",

}

Lindner, W & Hammerschmidt, F 2003, 'Enzymes in Organic Chemistry, 11:[1] Hydrolase-Catalyzed Resolution of a- and ß-Hydroxyphosphonates and Synthesis of Chiral, Non-Racemic ß-Aminophosphonic Acids', , Jg. 345, Nr. 12, S. 1287-1298.

Enzymes in Organic Chemistry, 11:[1] Hydrolase-Catalyzed Resolution of a- and ß-Hydroxyphosphonates and Synthesis of Chiral, Non-Racemic ß-Aminophosphonic Acids. / Lindner, Wolfgang; Hammerschmidt, Friedrich (Korresp. Autor*in).

in: , Band 345, Nr. 12, 2003, S. 1287-1298.

Veröffentlichungen: Beitrag in Fachzeitschrift › Artikel › Peer Reviewed

TY - JOUR

T1 - Enzymes in Organic Chemistry, 11:[1] Hydrolase-Catalyzed Resolution of a- and ß-Hydroxyphosphonates and Synthesis of Chiral, Non-Racemic ß-Aminophosphonic Acids

AU - Lindner, Wolfgang

AU - Hammerschmidt, Friedrich

N1 - Zeitschrift: Advanced Synthesis and CatalysisCoden: JPCHFAffiliations: Institut für Organische Chemie, Universität Wien, Währingerstraße 38, 1090 Wien, Austria; Institut für Analytische Chemie, Universität Wien, Währingerstraße 38, A-1090 Wien, AustriaAdressen: Hammerschmidt, F.; Institut für Organische Chemie; Universität Wien; Währingerstraße 38 1090 Wien, Austria; email: friedrich.hammerschmidt@univie.ac.atSource-File: ChemieErgScopus.csvImport aus Scopus: 2-s2.0-1642576230Importdatum: 09.01.2007 14:10:4622.10.2007: Datenanforderung 1934 (Import Sachbearbeiter)

PY - 2003

Y1 - 2003

N2 - The enantioselective acylation of racemic diisopropyl a- and ß-hydroxyphosphonates by hydrolases in t-butyl methyl ether with isopropenyl acetate as acyl donor is limited by the narrow substrate specificity of the enzymes. High enantiomeric excesses (up to 99%) were obtained for the acetates of (S)-diisopropyl 1-hydroxy-(2-thienyl)methyl-, 1-hydroxyethyl- and 1-hydroxyhexylphosphonate and (R)-diisopropyl 2-hydroxypropylphosphonate. The hydrolysis of a variety of ß- chloroacetoxyphosphonates by the lipase from Candida cylindracea and protease subtilisin in a biphasic system gives (S)-ß-hydroxyphosphonates (ee 51-92%) enantioselectively. (S)-2-Phenyl-2-hydroxyethyl- and (S)-3-methyl-2- hydroxybutylphosphonates (ee 96% and 99%, respectively) were transformed into (R)-2-aminophosphonic acids of the same ee.

AB - The enantioselective acylation of racemic diisopropyl a- and ß-hydroxyphosphonates by hydrolases in t-butyl methyl ether with isopropenyl acetate as acyl donor is limited by the narrow substrate specificity of the enzymes. High enantiomeric excesses (up to 99%) were obtained for the acetates of (S)-diisopropyl 1-hydroxy-(2-thienyl)methyl-, 1-hydroxyethyl- and 1-hydroxyhexylphosphonate and (R)-diisopropyl 2-hydroxypropylphosphonate. The hydrolysis of a variety of ß- chloroacetoxyphosphonates by the lipase from Candida cylindracea and protease subtilisin in a biphasic system gives (S)-ß-hydroxyphosphonates (ee 51-92%) enantioselectively. (S)-2-Phenyl-2-hydroxyethyl- and (S)-3-methyl-2- hydroxybutylphosphonates (ee 96% and 99%, respectively) were transformed into (R)-2-aminophosphonic acids of the same ee.

M3 - Article

VL - 345

SP - 1287

EP - 1298

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

SN - 1615-4150

IS - 12

ER -

Lindner W, Hammerschmidt F. Enzymes in Organic Chemistry, 11:[1] Hydrolase-Catalyzed Resolution of a- and ß-Hydroxyphosphonates and Synthesis of Chiral, Non-Racemic ß-Aminophosphonic Acids. . 2003;345(12):1287-1298.