67951-43-3

Usage

InChI:InChI=1/C5H8O3/c1-2-3-4(6)5(7)8/h2,4,6H,1,3H2,(H,7,8)

Upstream product

• 4704-23-8 glycolic acid allyl ester 
• 106-95-6 allyl bromide 
• 563-96-2 2,2-dihydroxyacetic acid 
• 4746-62-7 2-amino-2-hydroxyacetic acid 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 41453-55-8 4-hydroxy-2-oxopentanoic acid 
• 20406-62-6 2-oxopent-4-enoic acid 
• 24850-33-7 allyltributylstanane 
• 298-12-4 Glyoxilic acid 
• 156366-39-1 2-hydroxy-2,4-hexadiene-1,6-dioate 
• 96488-09-4 1-((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-but-3-en-1-ol 
• 39149-86-5 2-bromopent-4-enoic acid ethyl ester 
• 29119-70-8 Ethyl 2-chloro-4-pentenoate 

Downstream Products

• 617-31-2 2-hydroxyvaleric acid 
• 410098-23-6 5-allyl-2,2-dimethyl-1,3-dioxolan-4-one 
• 851626-21-6 2-(4-methoxybenzyloxy)pent-4-enoic acid 
• 36157-55-8 2-(4-Chlor-benzoyloxy)-4-pentensaeure 
• 626-99-3 1,3-butadiene-1-carboxylic acid 
• 81357-28-0 (RS)-3-hydroxy-4-pentenoic acid 
• 851626-39-6 (2RS,1'S,2'E) 2-(4-methoxybenzyloxy)pent-4-enoic acid 4'-(tert-butyl(diphenyl)silyloxy)-1'-methylbut-2'-enyl ester 
• 1011481-78-9 (2RS)-2-hydroxy-4-pentenoyl-Ala-Phe-Ile-NHAll 

Relevant academic research and scientific papers

Ketonization of 2-hydroxy-2,4-pentadienoate by 4-oxalocrotonate tautomerase: Implications for the stereochemical course and the mechanism

4-Oxalocrotonate tautomerase (EC 5.3.2-; 4-OT), an enzyme involved in the bacterial degradation of catechol to intermediates in the Krebs cycle, catalyzes the ketonization of 2-hydroxymuconate (1) to the α,β-unsaturated ketone (E)-2-oxo-3-hexenedioate (2). Kinetic studies on 4-OT suggest that the enzyme is an isomerase and catalyzes the transformation of (E)-2-oxo-4-hexenedioate (3) to 2 through the intermediacy of 1. Isomerases can proceed by either a "one-base" or a "two-base" mechanism. The overall stereochemical course of an isomerase reaction can be used to distinguish between these two mechanisms. The stereochemical analysis of the 4-OT reaction presents a challenge because the proposed substrate, 3, cannot be synthesized or isolated. This complication is circumvented by utilizing strategies based on the expected stereospecific partitioning of 1 and related dienols in 2H2O. It was previously determined that 4-OT ketonizes 1 to (5S)-[5-2H]2. Because it was not possible to obtain sufficient quantities of [3-2H]3 for stereochemical analysis, an alternate substrate for 4-OT, 2-hydroxy-2,4-pentadienoate (4), was used in order to determine the stereochemistry of deuterium incorporation at the 3-position. The dienol 4 is ketonized rapidly by 4-OT to the β,γ-unsaturated ketone 2-oxo-4-pentenoate (5) before a much slower conversion to its α,β-isomer, 2-oxo-3-pentenoate (6). This behavior allows for the accumulation of 5 in solution. In order to assign the stereochemistry, the 4-OT-catalyzed ketonization of 4 was performed in 2H2O. The product, [3-2H]5, was trapped with NaBH4, processed to [3-2H]malate by chemical and enzymatic degradative procedures, and analyzed by 1H NMR spectroscopy. It was concluded that 4-OT ketonizes 4 stereoselectively to (3R)-2-oxo-[3-2H]-4-pentenoate. This result and the previous stereochemical finding indicate that the isomerization of 3 to 2 is predominantly a suprafacial process suggesting that 4-OT proceeds by a one-base mechanism.

One-Shot Intrablock Cross-Linking of Linear Diblock Copolymer to Realize Janus-Shaped Single-Chain Nanoparticles

Developing an efficient and versatile process to transform a single linear polymer chain into a shape-defined nanoobject is a major challenge in the fields of chemistry and nanotechnology to replicate sophisticated biological functions of proteins and nucleic acids in a synthetic polymer system. In this study, we performed one-shot intrablock cross-linking of linear block copolymers (BCPs) to realize single-chain nanoparticles (SCNPs) with two chemically compartmentalized domains (Janus-shaped SCNPs). Detailed structural characterizations of the Janus-shaped SCNP composed of polystyrene-block-poly(glycolic acid) revealed its compactly folded conformation and compartmentalized block localization, similar to the self-folded tertiary structures of natural proteins. Versatility of the one-shot intrablock cross-linking was demonstrated using several different BCP precursors. In addition, the Janus-shaped SCNP produce miniscule microphase-separated structures.

Generation of a Heteropolycyclic and sp3-Rich Scaffold for Library Synthesis from a Highly Diastereoselective Petasis/Diels–Alder and ROM–RCM Reaction Sequence

Efficient access to diverse screening compounds with desirable, lead-like properties can be a bottleneck in early drug discovery and chemical biology. Herein we present an efficient, rapid route to three structurally distinct classes of compounds (A–C) from a single precursor, which in turn is available through a one-pot Petasis 3-component reaction/Diels–Alder cascade reaction. We demonstrate the versatility of the approach through the synthesis of 35 exemplary compounds from the three classes, as well as by the production of 2188 final compounds, which have been included in the Joint European Compound Library of the European Lead Factory.

Diastereoselective synthesis of novel heterocyclic scaffolds through tandem Petasis 3-component/intramolecular Diels-Alder and ROM-RCM reactions

A high-yielding, stereoselective and extraordinarily complexity-generating Petasis 3-component/intramolecular Diels-Alder reaction has been developed. In combination with ROM-RCM, rapid access to complex sp3-rich heterocyclic scaffolds amenable

MICROORGANISMS FOR PRODUCING 4C-5C COMPOUNDS WITH UNSATURATION AND METHODS RELATED THERETO

The invention provides a non-naturally occurring microbial organism having a butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol, pathway. The microbial organism contains at least one exogenous nucleic acid encoding an enzyme in a pathway. The invention additionally provides a method for producing butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol,. The method can include culturing a butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol-producing microbial organism, where the microbial organism expresses at least one exogenous nucleic acid encoding a pathway enzyme in a sufficient amount, and under conditions and for a sufficient period of time to produce butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol.

Electrochemical allylation of carbonyl compounds in aqueous electrolyte catalyzed by zinc

A highly efficient electroallylation of carbonyl compounds in aqueous electrolyte in a divided cell with a catalytic amount of zinc consumption is reported.

Zn-mediated electrochemical allylation of aldehydes in aqueous ammonia

An efficient electrosynthesis of homoallylic alcohols from allylic bromides and aldehydes in aqueous ammonia is achieved in an undivided cell fitted with a pair of zinc electrodes.

Regio- and stereochemical aspects in synthesis of 2-allyl derivatives of glycolic, mandelic and lactic acids and their iodocyclisations to 3-hydroxy-3,4-dihydrofuran-2(5H)-ones

Glyoxalic, phenylglyoxalic and pyruvic acids 1a-c undergo regio- and diastereoselective indium mediated allylations with allyl and cinnamyl bromides and ethyl 4-bromocrotonate to provide respective 2-allyl-, 2-(1-phenylallyl)- and 2-[(1-ethoxycarbonyl)all

Direct synthesis of unprotected α-amino acids via allylation of hydroxyglycine

Hydroxyglycine, the ammonia adduct of glyoxylic acid, was found to react with various allylboronates in the presence of triethylamine in methanol to give unprotected α-amino acids directly with high stereoselectivity. For instance, the reactions with (E)- and (Z)-crotylboronates afforded the corresponding anti- and syn-crotylated products (isoleucine and alloisoleucine after hydrogenation) with high diastereoselectivity, respectively. Interestingly, it was found that isomerization of the products (γ-adducts to α-adducts) occurred under the reaction conditions in some cases. Control experiments have suggested that the isomerization took place via 2-aza (or azonia) Cope rearrangement of imines derived from γ-adducts and glyoxylic acid.

Efficient allylation of aldehydes promoted by carboxylic acids

A variety of carboxylic acids have been screened for mediating the allylation of aldehydes with allytributyltin in different solvents. A novel, general, and practical method of allylation of aldehydes promoted by carboxylic acids under mild reaction condi