Efficient Chemoenzymatic Synthesis of (2,3)-3-Hydroxy-3-Methylproline, a Key Fragment in Polyoxypeptin A and FR225659

Overview

Journal Tetrahedron

Specialty Chemistry

Date 2019 Dec 31

PMID 31885405

Citations 7

Authors

Xiao Zhang

Hans Renata

Affiliations

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Abstract

We report an efficient synthesis of protected (2,3)-3-hydroxy-3-methylproline that proceeds in three steps with complete stereoselectivity. This route represents a significant improvement over previous approaches to this noncanonical amino acid. Key to this success is the development of a one-pot chemoenzymatic procedure for the preparation of (2,3)-3- methylproline from L-isoleucine. This work lays the foundation for future chemoenzymatic syntheses of polyoxypeptin A and FR225659.

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References

Mattay J, Huttel W . Pipecolic Acid Hydroxylases: A Monophyletic Clade among cis-Selective Bacterial Proline Hydroxylases that Discriminates l-Proline. Chembiochem. 2017; 18(15):1523-1528. DOI: 10.1002/cbic.201700187. View

Thomas J, Ayling A, Baneyx F . Molecular chaperones, folding catalysts, and the recovery of active recombinant proteins from E. coli. To fold or to refold. Appl Biochem Biotechnol. 1997; 66(3):197-238. DOI: 10.1007/BF02785589. View

Zhang X, King-Smith E, Renata H . Total Synthesis of Tambromycin by Combining Chemocatalytic and Biocatalytic C-H Functionalization. Angew Chem Int Ed Engl. 2018; 57(18):5037-5041. DOI: 10.1002/anie.201801165. View

Umezawa K, Nakazawa K, Ikeda Y, Naganawa H, Kondo S . Polyoxypeptins A and B Produced by Streptomyces: Apoptosis-Inducing Cyclic Depsipeptides Containing the Novel Amino Acid (2S,3R)-3-Hydroxy-3-methylproline. J Org Chem. 2001; 64(9):3034-3038. DOI: 10.1021/jo981512n. View

Li F, Zhang X, Renata H . Enzymatic CH functionalizations for natural product synthesis. Curr Opin Chem Biol. 2018; 49:25-32. PMC: 6437013. DOI: 10.1016/j.cbpa.2018.09.004. View

Hatori H, Zenkoh T, Kobayashi M, Ohtsu Y, Shigematsu N, Setoi H . FR225659-binding proteins: identification as serine/threonine protein phosphatase PP1 and PP2A using high-performance affinity beads. J Antibiot (Tokyo). 2004; 57(7):456-61. DOI: 10.7164/antibiotics.57.456. View

Reddy L, Subba Reddy B, Corey E . Efficient method for selective introduction of substituents as C5 of isoleucine and other alpha-amino acids. Org Lett. 2006; 8(13):2819-21. DOI: 10.1021/ol060952v. View

Ohtsu Y, Sasamura H, Tsurumi Y, Yoshimura S, Takase S, Hashimoto M . The novel gluconeogenesis inhibitors FR225659 and related compounds that originate from Helicomyces sp. No. 19353. I. Taxonomy, fermentation, isolation and physico-chemical properties. J Antibiot (Tokyo). 2003; 56(8):682-8. DOI: 10.7164/antibiotics.56.682. View

Du Y, Wang Y, Huang T, Tao M, Deng Z, Lin S . Identification and characterization of the biosynthetic gene cluster of polyoxypeptin A, a potent apoptosis inducer. BMC Microbiol. 2014; 14:30. PMC: 3943440. DOI: 10.1186/1471-2180-14-30. View

10.

Jurica E, Wu X, Williams K, Hernandez A, Nirschl D, Rampulla R . Discovery of Pyrrolidine-Containing GPR40 Agonists: Stereochemistry Effects a Change in Binding Mode. J Med Chem. 2017; 60(4):1417-1431. DOI: 10.1021/acs.jmedchem.6b01559. View

11.

Sato H, Yoshida M, Murase H, Nakagawa H, Doi T . Combinatorial Solid-Phase Synthesis and Biological Evaluation of Cyclodepsipeptide Destruxin B as a Negative Regulator for Osteoclast Morphology. ACS Comb Sci. 2016; 18(9):590-5. DOI: 10.1021/acscombsci.6b00076. View

12.

Ghislieri D, Green A, Pontini M, Willies S, Rowles I, Frank A . Engineering an enantioselective amine oxidase for the synthesis of pharmaceutical building blocks and alkaloid natural products. J Am Chem Soc. 2013; 135(29):10863-9. DOI: 10.1021/ja4051235. View

13.

Li L, Tang M, Tang S, Gao S, Soliman S, Hang L . Genome Mining and Assembly-Line Biosynthesis of the UCS1025A Pyrrolizidinone Family of Fungal Alkaloids. J Am Chem Soc. 2018; 140(6):2067-2071. PMC: 5817883. DOI: 10.1021/jacs.8b00056. View

14.

Zwick 3rd C, Renata H . Remote C-H Hydroxylation by an α-Ketoglutarate-Dependent Dioxygenase Enables Efficient Chemoenzymatic Synthesis of Manzacidin C and Proline Analogs. J Am Chem Soc. 2017; 140(3):1165-1169. DOI: 10.1021/jacs.7b12918. View