11. Isofagomine is a non-natural product design and synthesized in 1994, which inhibits the activity or veral enzymes. Recently, an asymmetric synthesis was reported (Kulkarni Tetrahedron: Asymmetry 2012, 1234). One of the intermediates in Kulkarny's synthesis is a diol, synthesized by a dinydroxyklation of an alcohol as it's shown in the reaction scheme. The reaction is carried out in the presence of a catalysts under the conditions indicated. Assign the stereochemistry to the new chiral centers produced after the dihydroxylation and tell where the addition took place in each of the two carbons in the double bond of the substrate (Re/Si face). AD mix-B, 1:1 BUOH/H2O, 0 °C/12h OH N3 N3 Wort a BnO ÕH BnO
11. Isofagomine is a non-natural product design and synthesized in 1994, which inhibits the activity or veral enzymes. Recently, an asymmetric synthesis was reported (Kulkarni Tetrahedron: Asymmetry 2012, 1234). One of the intermediates in Kulkarny's synthesis is a diol, synthesized by a dinydroxyklation of an alcohol as it's shown in the reaction scheme. The reaction is carried out in the presence of a catalysts under the conditions indicated. Assign the stereochemistry to the new chiral centers produced after the dihydroxylation and tell where the addition took place in each of the two carbons in the double bond of the substrate (Re/Si face). AD mix-B, 1:1 BUOH/H2O, 0 °C/12h OH N3 N3 Wort a BnO ÕH BnO
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Catalysis and Enzymatic Reactions
Catalysis is the kind of chemical reaction in which the rate (speed) of a reaction is enhanced by the catalyst which is not consumed during the process of reaction and afterward it is removed when the catalyst is not used to make up the impurity in the product. The enzymatic reaction is the reaction that is catalyzed via enzymes.
Lock And Key Model
The lock-and-key model is used to describe the catalytic enzyme activity, based on the interaction between enzyme and substrate. This model considers the lock as an enzyme and the key as a substrate to explain this model. The concept of how a unique distinct key only can have the access to open a particular lock resembles how the specific substrate can only fit into the particular active site of the enzyme. This is significant in understanding the intermolecular interaction between proteins and plays a vital role in drug interaction.
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Transcribed Image Text:**Isofagomine Synthesis Overview**
**Chemical Process and Stereochemistry:**
Isofagomine is a non-natural compound designed and synthesized in 1994, known for inhibiting the activity of several enzymes. A recent report discussed an asymmetric synthesis approach for isofagomine (Kulkarni, Tetrahedron: Asymmetry, 2012, 1234). An intermediate in Kulkarni's synthesis is a diol, developed through the dihydroxylation of an alcohol as illustrated in the reaction scheme below.
The reaction occurs using catalysts under specific conditions. This process involves assigning stereochemistry to the new chiral centers formed following dihydroxylation and identifying the position of addition on each of the two carbons in the substrate's double bond (Re/Si face).
**Reaction Scheme Description:**
- **Starting Material:** An alkene-containing compound with an azide group (N₃), a benzyl ether (BnO), and a cyclohexene ring.
- **Reagents and Conditions:** AD mix-β, in a 1:1 tert-butanol (tBuOH) and water (H₂O) solvent mixture, at 0°C over 12 hours.
- **Product:** The resulting molecule is a diol, which now has two new hydroxyl groups (OH) added. The stereochemistry around these new chiral centers is specified with wedges and dashes, indicating the three-dimensional configuration.
This synthesis method aims to deliver added precision in the stereochemical outcomes, crucial for the desired biological activity of isofagomine.
Expert Solution
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The given reaction results in the following transformation of the molecule,
The product has two new chiral centers.
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