Asymmetric Self‐ and Cross‐Aldol Reactions of Glycolaldehyde Catalyzed by <scp>D</scp>‐Fructose‐6‐phosphate Aldolase

Garrabou, Xavier; Castillo, José A. García del; Guérard-Hélaine, Christine; Parella, Teodor; Joglar, Jesús; Lemaire, Marielle; Clapés, Pere

doi:10.1002/anie.200902065

Cited by 119 publications

(82 citation statements)

References 42 publications

(48 reference statements)

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“…Interestingly, the aldol addition of DHA to GO proceeded in 80% aldehyde conversion to d-xylulose (Scheme 8.30) [6]. This was the most striking result since using FSA wild type, and d-threose was exclusively formed arising from the homo-aldol addition reaction of GO [106].…”

Section: D-fructose-6-phosphate Aldolase and Transaldolase B Phe178tymentioning

confidence: 67%

“…The use of DHA for the preparation of unphosphorylated targets simplifies the synthetic strategy avoiding the manipulation of the phosphate moiety and fostering the methodology to industrial applications. Most importantly, the FSA In terms of V m /K M , the FSA wild-type reactivity for the donors follows the order HA > GO >> DHA [106], and hence the DHA was the worse donor, which was also noticed when comparing the conversions of aldol additions of HA and DHA to the same aldehydes [104,105].…”

Section: D-fructose-6-phosphate Aldolase and Transaldolase B Phe178tymentioning

confidence: 94%

“…The complementary behavior of FSA and TalB mutant was recently exploited to prepare a collection of deoxygenated carbohydrates using FSA for HA and HB aldol additions and TalB Phe178Tyr with DHA (Table 8.4) [6,111]. Interestingly, FSA Ala129Ser and TalB Phe178Tyr render mainly the cross-aldol reaction product of DHA and GO, whereas FSA wild type provides exclusively the self-aldolization product, d-threose [106]. FSA wild type also accomplishes cross-aldol additions of GO as acceptor with HA as donor [105].…”

Section: D-fructose-6-phosphate Aldolase and Transaldolase B Phe178tymentioning

confidence: 99%

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Enzyme‐Catalyzed Aldol Additions

Clapés¹,

Joglar²

2013

Modern Methods in Stereoselective Aldol Reactions

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Section: D-fructose-6-phosphate Aldolase and Transaldolase B Phe178tymentioning

confidence: 67%

Section: D-fructose-6-phosphate Aldolase and Transaldolase B Phe178tymentioning

confidence: 94%

Section: D-fructose-6-phosphate Aldolase and Transaldolase B Phe178tymentioning

confidence: 99%

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Enzyme‐Catalyzed Aldol Additions

Clapés¹,

Joglar²

2013

Modern Methods in Stereoselective Aldol Reactions

Self Cite

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“…Recently, Yamaguchi et al have successfully exploited this in their attempt to couple formaldehyde to triose sugars, forming α-hydroxy-γ-butyrolactone (HBL), a cyclic C 4 -α-hydroxy ester that fi nds its use as a synthetic intermediate in pharmaceutical chemistry [ 37 , 129 ]. A similar approach was followed earlier for the coupling of formaldehyde to GA with D -fructose -6 -phosphate aldolase [ 130 ]. In Yamaguchi's work, Sn halides were the most active catalysts, yielding up to 70 % HBL after 3 h at 140 °C in 1,4-dioxane when using 14 mol% SnCl 4 .…”

Section: Cross Coupling Of Small Carbohydratesmentioning

confidence: 90%

Advances in the Conversion of Short-Chain Carbohydrates: A Mechanistic Insight

Clercq

Dusselier

Sels

2016

Green Chemistry and Sustainable Technology

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This chapter discusses recent insights in the conversion of short carbohydrates, viz., sugars containing four or less carbon atoms. Rather than summarizing product yields from such sugars and reported catalysts for the conversions, the focus lies on understanding the underlying mechanisms. These short carbohydrates can lead to a broad spectrum of products, ranging from platform chemicals such as lactic acid and ethylene glycol to high-value chemicals such as α-hydroxy-γ-butyrolactone and even fuels. Different synthesis strategies of these short carbohydrates include (1) a top -down approach from mono-or polysaccharides and (2) a selective bottom -up synthesis route from formaldehyde. Lewis acids play a major role in carbohydrate chemistry, and among these, Sn-based catalysts often show the highest activity. Whether dioses, trioses, or tetroses are used as substrate, Sn is able to convert them effi ciently into α-hydroxy acids or esters, which are useful building blocks for renewable polyesters. Other reaction types such as isomerization, hydrogenation, and cross couplings are discussed briefl y as well. Glycerol and glyoxal are no sugars, but their chemistry shows great resemblance to that of carbohydrates. Therefore, these compounds are also briefl y accounted for in this chapter.

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“…The development of asymmetric aldol reaction catalysts remains an active area of research, and numerous successful organocatalysts and aldolases have been described in recent years (Garrabou et al, 2009;Mase et al, 2006). Although traditional catalysts exhibit high efficiency and enantioselectivity, the development of environmentally friendly and cost-efficient methods for C-C bond formation still presents a significant challenge (Mestres, 2004).…”

Section: Introductionmentioning

confidence: 99%