Synthesis of allysine ethylene acetal using phenylalanine dehydrogenase from Thermoactinomyces intermedius

Allysine ethylene acetal [(S)-2-amino-5-(1,3-dioxolan-2-yl)-pentanoic acid ( 2)] was prepared from the corresponding keto acid by reductive amination using phenylalanine dehydrogenase (PDH) from Thermoactinomyces intermedius ATCC 33205. Glutamate, alanine, and leucine dehydrogenases, and PDH from Sp...

Full description

Saved in:
Bibliographic Details
Published in:Enzyme and microbial technology 2000-03, Vol.26 (5), p.348-358
Main Authors: Hanson, Ronald L, Howell, Jeffrey M, LaPorte, Thomas L, Donovan, Mary Jo, Cazzulino, Dana L, Zannella, Valerie, Montana, Michael A, Nanduri, Venkata B, Schwarz, Steven R, Eiring, Ronald F, Durand, Susan C, Wasylyk, John M, Parker, William L, Liu, Mark S, Okuniewicz, Francis J, Chen, Bang-Chi, Harris, John C, Natalie, Kenneth J, Ramig, Keith, Swaminathan, Shankar, Rosso, Victor W, Pack, Shawn K, Lotz, Bruce T, Bernot, Peter J, Rusowicz, Andrew, Lust, David A, Tse, Kai S, Venit, John J, Szarka, Laszlo J, Patel, Ramesh N
Format: Article
Language:English
Subjects:
Allysine ethylene acetal
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Escherichia coli
Formate dehydrogenase
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
Phenylalanine dehydrogenase
Pichia pastoris
Thermoactinomyces intermedius
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Allysine ethylene acetal [(S)-2-amino-5-(1,3-dioxolan-2-yl)-pentanoic acid ( 2)] was prepared from the corresponding keto acid by reductive amination using phenylalanine dehydrogenase (PDH) from Thermoactinomyces intermedius ATCC 33205. Glutamate, alanine, and leucine dehydrogenases, and PDH from Sporosarcina species (listed in order of increasing effectiveness) also gave the desired amino acid but were less effective. The reaction requires ammonia and NADH. NAD produced during the reaction was recyled to NADH by the oxidation of formate to CO 2 using formate dehydrogenase (FDH). PDH was produced by growth of T. intermedius ATCC 33205 or by growth of recombinant Escherichia coli or Pichia pastoris expressing the Thermoactinomyces enzyme. Using heat-dried T. intermedius as a source of PDH and heat-dried Candida boidinii SC13822 as a source of FDH , reaction yields averaged 84 M%, and ee was >98%, but production of T. intermedius could not be scaled up. Using heat-dried recombinant E. coli as a source of PDH and heat-dried Candida boidinii as a source of FDH, 197 kg of 2 was produced in three batches with an average yield of 91 M% and ee > 98%. In a third generation process, heat-dried methanol-grown P. pastoris expressing endogenous FDH and recombinant Thermoactinomyces PDH was used to produce 15 kg of 2 with a yield of 97 M% and >98% ee.
ISSN:0141-0229
1879-0909
DOI:10.1016/S0141-0229(99)00175-1