Fructose-6-phosphate aldolase in organic synthesis: Preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays

José A. Castillo; Jordi Calveras; Josefina Casas; Montserrat Mitjans; M. Pilar Vinardell; Teodor Parella; Tomoyuki Inoue; Georg A. Sprenger; Jesús Joglar; Pere Clapés

doi:https://doi.org/10.1021/ol0625482

Fructose-6-phosphate aldolase in organic synthesis: Preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays

José A. Castillo, Jordi Calveras, Josefina Casas, Montserrat Mitjans, M. Pilar Vinardell, Teodor Parella, Tomoyuki Inoue, Georg A. Sprenger, Jesús Joglar, Pere Clapés

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

115 Citations (Scopus)

Abstract

(Chemical Equation Presented) D-Fructose-6-phosphate aldolase (FSA) mediates a novel straightforward two-step chemo-enzymatic synthesis of D-fagomine and some of its N-alkylated derivatives in 51% isolated yield and 99% de. The key step is the FSA-catalyzed aldol addition of simple dihydroxyacetone (DHA) to N-Cbz-3-aminopropanal. The use of FSA greatly simplifies the enzymatic procedures that used dihydroxyacetonephosphate or DHA/esters. Some N-alkyl derivatives synthesized elicited antifungal and antibacterial activity as well as enhanced inhibitory activity, and selectivity against β-galactosidase and α-glucosidase. © 2006 American Chemical Society.

Original language	English
Pages (from-to)	6067-6070
Journal	Organic Letters
Volume	8
DOIs	https://doi.org/10.1021/ol0625482
Publication status	Published - 21 Dec 2006

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Castillo, José A. ; Calveras, Jordi ; Casas, Josefina ; Mitjans, Montserrat ; Vinardell, M. Pilar ; Parella, Teodor ; Inoue, Tomoyuki ; Sprenger, Georg A. ; Joglar, Jesús ; Clapés, Pere. / Fructose-6-phosphate aldolase in organic synthesis: Preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays. In: Organic Letters. 2006 ; Vol. 8. pp. 6067-6070.

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title = "Fructose-6-phosphate aldolase in organic synthesis: Preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays",

abstract = "(Chemical Equation Presented) D-Fructose-6-phosphate aldolase (FSA) mediates a novel straightforward two-step chemo-enzymatic synthesis of D-fagomine and some of its N-alkylated derivatives in 51% isolated yield and 99% de. The key step is the FSA-catalyzed aldol addition of simple dihydroxyacetone (DHA) to N-Cbz-3-aminopropanal. The use of FSA greatly simplifies the enzymatic procedures that used dihydroxyacetonephosphate or DHA/esters. Some N-alkyl derivatives synthesized elicited antifungal and antibacterial activity as well as enhanced inhibitory activity, and selectivity against β-galactosidase and α-glucosidase. {\textcopyright} 2006 American Chemical Society.",

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Fructose-6-phosphate aldolase in organic synthesis: Preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays. / Castillo, José A.; Calveras, Jordi; Casas, Josefina; Mitjans, Montserrat; Vinardell, M. Pilar; Parella, Teodor; Inoue, Tomoyuki; Sprenger, Georg A.; Joglar, Jesús; Clapés, Pere.

In: Organic Letters, Vol. 8, 21.12.2006, p. 6067-6070.

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

TY - JOUR

T1 - Fructose-6-phosphate aldolase in organic synthesis: Preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays

AU - Castillo, José A.

AU - Calveras, Jordi

AU - Casas, Josefina

AU - Mitjans, Montserrat

AU - Vinardell, M. Pilar

AU - Parella, Teodor

AU - Inoue, Tomoyuki

AU - Sprenger, Georg A.

AU - Joglar, Jesús

AU - Clapés, Pere

PY - 2006/12/21

Y1 - 2006/12/21

N2 - (Chemical Equation Presented) D-Fructose-6-phosphate aldolase (FSA) mediates a novel straightforward two-step chemo-enzymatic synthesis of D-fagomine and some of its N-alkylated derivatives in 51% isolated yield and 99% de. The key step is the FSA-catalyzed aldol addition of simple dihydroxyacetone (DHA) to N-Cbz-3-aminopropanal. The use of FSA greatly simplifies the enzymatic procedures that used dihydroxyacetonephosphate or DHA/esters. Some N-alkyl derivatives synthesized elicited antifungal and antibacterial activity as well as enhanced inhibitory activity, and selectivity against β-galactosidase and α-glucosidase. © 2006 American Chemical Society.

AB - (Chemical Equation Presented) D-Fructose-6-phosphate aldolase (FSA) mediates a novel straightforward two-step chemo-enzymatic synthesis of D-fagomine and some of its N-alkylated derivatives in 51% isolated yield and 99% de. The key step is the FSA-catalyzed aldol addition of simple dihydroxyacetone (DHA) to N-Cbz-3-aminopropanal. The use of FSA greatly simplifies the enzymatic procedures that used dihydroxyacetonephosphate or DHA/esters. Some N-alkyl derivatives synthesized elicited antifungal and antibacterial activity as well as enhanced inhibitory activity, and selectivity against β-galactosidase and α-glucosidase. © 2006 American Chemical Society.

U2 - https://doi.org/10.1021/ol0625482

DO - https://doi.org/10.1021/ol0625482

M3 - Article

VL - 8

SP - 6067

EP - 6070

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