Synthesis of a protected derivative of (2R,3R)-β-hydroxyaspartic acid suitable for Fmoc-based solid phase synthesis

Boyaud, France; Viguier, Bruno; Inguimbert, Nicolas

doi:10.1016/j.tetlet.2012.10.120

Cited by 18 publications

(23 citation statements)

References 21 publications

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“…Treatment of 5 with HBr in acetic acid (HOAc) afforded the corresponding bromoacetate. Acetate hydrolysis in acidic ethanol and bromide displacement with sodium azide in N , N -dimethylformamide (DMF) gave the alcohol ( 6 ) in 83% yield with 5:1 dr over three steps. , The azobenzene fragment ( 9 ) was prepared in good yield via a Mills reaction of aniline 7 and nitrosobenzene 8 and a sequential Appel reaction. The coupling between fragments 6 and 9 was then investigated.…”

Section: Resultsmentioning

confidence: 99%

Photoswitchable Inhibitor of a Glutamate Transporter

Cheng

Shchepakin

Kavanaugh

et al. 2017

ACS Chem. Neurosci.

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Excitatory amino acid transporters clear glutamate from the synaptic cleft and play a critical role in glutamatergic neurotransmission. Their differential roles in astrocytes, microglia, and neurons are poorly understood due in part to a lack of pharmacological tools that can be targeted to specific cells and tissues. We now describe a photoswitchable inhibitor, termed ATT, that interacts with the major mammalian forebrain transporters EAAT1-3 in a manner that can be reversibly switched between trans (high-affinity) and cis (low-affinity) configurations using light of different colors. In the dark, ATT competitively inhibited the predominant glial transporter EAAT2 with ∼200-fold selectivity over the neuronal transporter EAAT3. Brief exposure to 350 nm light reduced the steady-state blocker affinity by more than an order of magnitude. Illumination of EAAT2 complexed with ATT induced a corresponding increase in the blocker off-rate monitored in the presence of glutamate. ATT can be used to reversibly manipulate glutamate transporter activity with light and may be useful to gain insights into the dynamic physiological roles of glutamate transporters in the brain, as well as to study the molecular interactions of transporters with ligands.

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Section: Resultsmentioning

confidence: 99%

Photoswitchable Inhibitor of a Glutamate Transporter

Cheng

Shchepakin

Kavanaugh

et al. 2017

ACS Chem. Neurosci.

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“…Several other synthesis routes can be used to obtain these compounds and are referenced in the literature [57][58][59][60]. As part of the synthesis of laxaphycin B, Boyaud et al also had to synthesize 3hydroxyaspartic acid to graft its side chain on Rink Amide resin [61]. The synthesis starts with a cyclic sulfate 35 derived from dimethylester tartrate (Figure 18).…”

Section: Synthesis Of Hydroxylated Amino Acidsmentioning

confidence: 99%

Thirtieth Anniversary of the Discovery of Laxaphycins. Intriguing Peptides Keeping a Part of Their Mystery

et al. 2021

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Lipopeptides are a class of compounds generally produced by microorganisms through hybrid biosynthetic pathways involving non-ribosomal peptide synthase and a polyketyl synthase. Cyanobacterial-produced laxaphycins are examples of this family of compounds that have expanded over the past three decades. These compounds benefit from technological advances helping in their synthesis and characterization, as well as in deciphering their biosynthesis. The present article attempts to summarize most of the articles that have been published on laxaphycins. The current knowledge on the ecological role of these complex sets of compounds will also be examined.

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“…Although there are several strategies reported to construct HyAsp, few of them could be conveniently utilized to prepare suitable building blocks for this synthetic route. This includes the tedious route starting from tartaric acid, [8] non‐suitable side chain protection in the masked acyl cyanide reaction [9] and difficult observation of trans product in the Sharpless aminohydroxylation reaction [10] . Inspired by the Sardina's work, [11] herein we developed a concise synthetic route for selectively preparing 2 a or 2 b in five steps with 37–40 % overall yield (Scheme 1.…”

Section: Figurementioning

confidence: 99%

Total Synthesis of Malacidin A by β‐Hydroxyaspartic Acid Ligation‐Mediated Cyclization and Absolute Structure Establishment

et al. 2020

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The development of novel antibiotics is critical to combating the growing emergence of drug-resistant pathogens. Malacidin A is a new member of the calcium-dependent antibiotic (CDAs) family with activity against antibioticresistant pathogens. Its mode of action is distinct from classical CDAs. However, the absolute structure of malacidin A has not been established. Herein, the total syntheses of malacidin A and its analogues are reported by a combination of Fmocbased solid-phase peptide synthesis (SPPS) and b-hydroxyaspartic acid ligation-mediated peptide cyclization. The total synthesis enabled us to establish the absolute configuration of malacidin A, which is in agreement with those for natural malacidin A confirmed by advanced Marfeys analysis in our study.

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Synthesis of a protected derivative of (2R,3R)-β-hydroxyaspartic acid suitable for Fmoc-based solid phase synthesis

Cited by 18 publications

References 21 publications

Photoswitchable Inhibitor of a Glutamate Transporter

Photoswitchable Inhibitor of a Glutamate Transporter

Thirtieth Anniversary of the Discovery of Laxaphycins. Intriguing Peptides Keeping a Part of Their Mystery

Total Synthesis of Malacidin A by β‐Hydroxyaspartic Acid Ligation‐Mediated Cyclization and Absolute Structure Establishment

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