628292-19-3Relevant academic research and scientific papers
NUCLEIC ACID CONJUGATES AND USES THEREOF
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Paragraph 00386, (2018/03/09)
Provided herein are conjugates comprising targeting moieties such as sugars, folates and cell-penetrating peptides, which can be used for the improved delivery of agents (e.g., nucleic acids, such as oligonucleotides or mRNAs, or other agents) to cells. The invention provides conjugates and compounds comprising targeting moieties, methods for preparing the same, and intermediates useful in their preparation. In another aspect, the present invention provides formulations (e.g., pharmaceutical compositions) comprising the targetting moiety-containing conjugates and compounds. The present invention also provides methods for delivering agents (e.g., nucleic acids such as oligonucleotides or mRNAs) to a cell, methods for treating and/or preventing a disease or condition in a subject, and methods for modulating gene expression in a cell or a subject. Further, provided herein are kits comprising the conjugates, or formulations thereof; and kits for the preparation of conjugates described herein.
Boron/zinc exchange reaction in the diastereoselective arylation of N-protected L-prolinal
Martins, Bruna S.,Luedtke, Diogo S.
, p. 5364 - 5369 (2014/10/15)
The diastereoselective arylation of chiral, non-racemic, N-trityl-protected L-prolinal has been investigated. The reactive aryl groups were generated by a boron/zinc exchange reaction between arylboronic acids and diethylzinc. The reactions proceeded in a highly diastereoselective fashion, and the resulting amino alcohols possessing two vicinal stereocenters were obtained in diastereomeric ratios of >20:1, regardless of the substituent at the transferable aryl group. The diastereoselectivity of the reactions is believed to be the result of an energetically favored Felkin-Anh transition state, with the competing Cram-chelation pathway precluded due to the presence of the bulky N-trityl protecting group. Copyright
New class of bifunctional thioureas from l-proline: Highly enantioselective Michael addition of 1,3-dicarbonyls to nitroolefins
Vinayagam, Poopathy,Vishwanath, Manjunatha,Kesavan, Venkitasamy
, p. 568 - 577 (2014/05/06)
A new class of bifunctional tertiary amine thiourea was synthesized from l-proline. The reported thiourea is amenable to steric and electronic modifications at the stereogenic center bearing a thiourea moiety. Excellent enantioselectivity was obtained in the Michael addition of 2,4-pentanedione to various nitro olefins using the new organocatalyst. The construction of contiguous stereocenters via the Michael reaction of substituted 1,3-dicarbonyls to nitro olefins was also carried out with very good yield, enantioselectivity, and diastereoselectivity.
Fluorinated organocatalysts for the enantioselective epoxidation of enals: Molecular preorganisation by the fluorine-iminium ion Gauche effect
Tanzer, Eva-Maria,Zimmer, Lucie E.,Schweizer, W. Bernd,Gilmour, Ryan
, p. 11334 - 11342,9 (2020/08/31)
The fluorine-iminium ion gauche effect is triggered upon union of a secondary β-fluoroamine and an α,β-unsaturated aldehyde, providing a useful strategy for controlling the molecular topology of intermediates that are central to organocatalytic processes. The β-fluoroamine (S)-2-(fluorodiphenylmethyl)pyrrolidine (1) is an effective catalyst for the enantioselective epoxidation of α,β-unsaturated aldehydes. A process of structural editing has revealed that the efficiency of this catalyst is due to the (fluorodiphenyl)methyl group when it is embedded in a β-fluoroiminium motif. Epoxidations of challenging cyclic α,β-disubstituted, β,β-disubstituted and α,β,β-trisubstituted enals catalysed by 1 proceed with excellent levels of enantiocontrol (up to 98 % ee). Fluorine finesse. The β-fluoroamine (S)-2-(fluorodiphenylmethyl)pyrrolidine (1) is an effective catalyst for the enantioselective epoxidation of α,β-unsaturated aldehydes (see scheme). Application of this catalyst to challenging cyclic α,β-disubstituted enals, β,β-disubstituted enals, and an α,β,β-trisubstituted enal proceeds in a highly enantioselective fashion (up to 98 % ee). Copyright
N-Tritylprolinal: An Efficient Building Block for the Stereoselective Synthesis of Proline-Derived Amino Alcohols
Bejjani, Joseph,Chemla, Fabrice,Audouin, Max
, p. 9747 - 9752 (2007/10/03)
N-Tritylprolinal (prepared in four steps from L-proline) shows a very high Felkin diastereoselectivity in its reaction with various nucleophiles, leading to a straightforward and highly stereoselective access to syn-proline-derived amino alcohols.
