A Vinyl Sulfone‐Based Fluorogenic Probe Capable of Selective Labeling of PHGDH in Live Mammalian Cells

Pan, Sijun; Jang, Seyoung; Liew, Si Si; Fu, Jiaqi; Wang, Danyang; Lee, Jun-Seok; Yao, Shao Q.

doi:10.1002/ange.201710856

Cited by 14 publications

(4 citation statements)

References 33 publications

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“…NAD + -dependent enzyme 3-phosphoglycerate dehydrogenase (PHGDH) is the first and only rate-limiting enzyme in the serine and glycine de novo biosynthetic pathway [10]. It catalyzes glycolytic intermediate 3-phosphoglycerate (3-PG) transformed into 3-phosphohydroxypyruvate (3-PHP) [11,12]. Subsequent enzymatic reactions in the pathway convert 3-PHP to serine via transamination (PSAT1) and phosphate ester hydrolysis (PSPH).…”

Section: Introductionmentioning

confidence: 99%

The Role of D-3-Phosphoglycerate Dehydrogenase in Cancer

Zhao¹,

Fu²,

Du³

et al. 2020

Int. J. Biol. Sci.

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Serine, a non-essential amino acid, can be imported from the extracellular environment by transporters and de novo synthesized from glycolytic 3-phosphoglycerate (3-PG) in the serine biosynthetic pathway (SSP). It has been reported that active serine synthesis might be needed for the synthesis of proteins, lipids, and nucleotides and the balance of folate metabolism and redox homeostasis, which are necessary for cancer cell proliferation. Human D-3-phosphoglycerate dehydrogenase (PHGDH), the first and only rate-limiting enzyme in the de novo serine biosynthetic pathway, catalyzes the oxidation of 3-PG derived from glycolysis to 3-phosphohydroxypyruvate (3-PHP). PHGDH is highly expressed in tumors as a result of amplification, transcription, or its degradation and stability alteration, which dysregulates the serine biosynthesis pathway via metabolic enzyme activity to nourish tumors. And some recent researches reported that PHGDH promoted some tumors growth via non-metabolic way by upregulating target cancer-promoting genes. In this article, we reviewed the type, structure, expression and inhibitors of PHGDH, as well as the role it plays in cancer and tumor resistance to chemotherapy.

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Section: Introductionmentioning

confidence: 99%

The Role of D-3-Phosphoglycerate Dehydrogenase in Cancer

Zhao¹,

Fu²,

Du³

et al. 2020

Int. J. Biol. Sci.

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“…Second, when the sensor is activated by the enzyme, its fluorescence should be amplified, or its fluorescence emission wavelength should be shifted, resulting in a change in fluorescence (i.e., enabling real-time monitoring). 8 The Bigger Picture…”

Section: Introductionmentioning

confidence: 99%

Sensors for In Situ Real-Time Fluorescence Imaging of Enzymes

Lee

et al. 2020

Chem

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“…7 Recently, vinyl sulfones are also used as a fluorogenic probe for selective labeling of live cells. 8 Given its importance, considerable amounts of efforts are devoted to their synthesis (Scheme 1A). 2a,7,9 Classically, vinyl sulfones are synthesized via Knoevenagel condensation of aldehydes with sulfonylacetic acids followed by decarboxylation, 9c Horner−Wadsworth− Emmons reactions of sulfonyl phosphonates and carbonyls, 7 βelimination of halo-or selenosulfones, 9d and oxidation of the corresponding sulfides 9e and recently by cross-coupling of a sulfonyl source with an alkene or alkynes (Scheme 1A).…”

Section: ■ Introductionmentioning

confidence: 99%

Manganese-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Sulfones: A Tool To Access Highly Substituted Vinyl Sulfones

2018

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The development of first-row-transition-metal catalysts that can match with the reactivities of the noble metals is considered to be challenging yet very much a desirable goal in homogeneous catalysis. It has become even more fascinating to develop processes where these metals show a unique reactivity and selectivity than their higher congeners. Herein, we report on the catalytic activity of a pincer complex of the abundant earth metal manganese for an unprecedented acceptorless dehydrogenative coupling of alkyl sulfones with alcohols. Thus, highly functionalized vinyl sulfones were obtained in moderate to good yields. Both benzylic and aliphatic alcohols could be utilized, and several functional groups including bromides and iodides are tolerated under the reaction conditions. The reaction is environmentally benign, producing dihydrogen and water as byproducts. Preliminary mechanistic experiments involving kinetic, deuterium-labeling, and NMR experiments were performed.

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A Vinyl Sulfone‐Based Fluorogenic Probe Capable of Selective Labeling of PHGDH in Live Mammalian Cells

Cited by 14 publications

References 33 publications

The Role of D-3-Phosphoglycerate Dehydrogenase in Cancer

The Role of D-3-Phosphoglycerate Dehydrogenase in Cancer

Sensors for In Situ Real-Time Fluorescence Imaging of Enzymes

Manganese-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Sulfones: A Tool To Access Highly Substituted Vinyl Sulfones

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