Matches in SemOpenAlex for { <https://semopenalex.org/work/W4313456443> ?p ?o ?g. }
Showing items 1 to 81 of
81
with 100 items per page.
- W4313456443 abstract "The syntheses are reported of Nϵ-(2,2,2-trifluoroethyl)-D, L-lysine (tFK) and Nζ-(2,2,2-trifluoroethyl)-D, L-homolysine (tFK+1) from amino alcohols HO−(CH2)n−NH2. The syntheses involve reductive amination, Appel bromination, and the stereoselective bond formation between Cα of the amino acid and the fluorinated alkyl chain in the Schöllkopf bislactim amino acid synthesis. The methyl esters of the fluorinated amino acids are the relevant substrates for oligopeptide synthesis. With the R-Schöllkopf reagent, we stereoselectively generated methyl Nϵ-boc-Nϵ-(2,2,2-trifluoroethyl)-L-lysinate and methyl Nζ-boc-Nζ-(2,2,2-trifluoroethyl)-L-homolysinate. Products and intermediates were characterized by 1H NMR, 13C NMR, COSY, HSQC, and LCMS. A variety of N-functionality may be introduced by reacting hemiacetals with different appendages. This fluorine modification reduces the sidechain N-basicity by combined -I effect of the three fluorines. This effect increases the [amine]/[ammonium ion] ratio of the sidechain amine in lysine to facilitate carbamylation at lower pH conditions." @default.
- W4313456443 created "2023-01-06" @default.
- W4313456443 creator A5031892395 @default.
- W4313456443 creator A5053438967 @default.
- W4313456443 date "2022-12-20" @default.
- W4313456443 modified "2023-09-23" @default.
- W4313456443 title "Unnatural Lysines with Reduced Sidechain <i>N</i> ‐Basicity: Synthesis of <i>N</i> ‐trifluoroethyl Substituted Lysine and Homologs" @default.
- W4313456443 cites W1969340112 @default.
- W4313456443 cites W1984552018 @default.
- W4313456443 cites W1993599112 @default.
- W4313456443 cites W2026223990 @default.
- W4313456443 cites W2030642428 @default.
- W4313456443 cites W2036683036 @default.
- W4313456443 cites W2043821378 @default.
- W4313456443 cites W2044821751 @default.
- W4313456443 cites W2046385606 @default.
- W4313456443 cites W2057667175 @default.
- W4313456443 cites W2072837612 @default.
- W4313456443 cites W2082967831 @default.
- W4313456443 cites W2088497317 @default.
- W4313456443 cites W2125345882 @default.
- W4313456443 cites W2125410126 @default.
- W4313456443 cites W2137297265 @default.
- W4313456443 cites W2157484039 @default.
- W4313456443 cites W2344647967 @default.
- W4313456443 cites W2781736778 @default.
- W4313456443 cites W2811225767 @default.
- W4313456443 cites W29369270 @default.
- W4313456443 cites W3085464518 @default.
- W4313456443 cites W3209637409 @default.
- W4313456443 doi "https://doi.org/10.1002/slct.202203132" @default.
- W4313456443 hasPublicationYear "2022" @default.
- W4313456443 type Work @default.
- W4313456443 citedByCount "1" @default.
- W4313456443 countsByYear W43134564432023 @default.
- W4313456443 crossrefType "journal-article" @default.
- W4313456443 hasAuthorship W4313456443A5031892395 @default.
- W4313456443 hasAuthorship W4313456443A5053438967 @default.
- W4313456443 hasConcept C131779359 @default.
- W4313456443 hasConcept C155647269 @default.
- W4313456443 hasConcept C161790260 @default.
- W4313456443 hasConcept C178790620 @default.
- W4313456443 hasConcept C181647583 @default.
- W4313456443 hasConcept C185592680 @default.
- W4313456443 hasConcept C2776016237 @default.
- W4313456443 hasConcept C2779938440 @default.
- W4313456443 hasConcept C40875361 @default.
- W4313456443 hasConcept C515207424 @default.
- W4313456443 hasConcept C55493867 @default.
- W4313456443 hasConcept C71240020 @default.
- W4313456443 hasConceptScore W4313456443C131779359 @default.
- W4313456443 hasConceptScore W4313456443C155647269 @default.
- W4313456443 hasConceptScore W4313456443C161790260 @default.
- W4313456443 hasConceptScore W4313456443C178790620 @default.
- W4313456443 hasConceptScore W4313456443C181647583 @default.
- W4313456443 hasConceptScore W4313456443C185592680 @default.
- W4313456443 hasConceptScore W4313456443C2776016237 @default.
- W4313456443 hasConceptScore W4313456443C2779938440 @default.
- W4313456443 hasConceptScore W4313456443C40875361 @default.
- W4313456443 hasConceptScore W4313456443C515207424 @default.
- W4313456443 hasConceptScore W4313456443C55493867 @default.
- W4313456443 hasConceptScore W4313456443C71240020 @default.
- W4313456443 hasFunder F4320309568 @default.
- W4313456443 hasIssue "48" @default.
- W4313456443 hasLocation W43134564431 @default.
- W4313456443 hasOpenAccess W4313456443 @default.
- W4313456443 hasPrimaryLocation W43134564431 @default.
- W4313456443 hasRelatedWork W1987755785 @default.
- W4313456443 hasRelatedWork W2022537202 @default.
- W4313456443 hasRelatedWork W2075761790 @default.
- W4313456443 hasRelatedWork W2137039563 @default.
- W4313456443 hasRelatedWork W2339961519 @default.
- W4313456443 hasRelatedWork W2400895839 @default.
- W4313456443 hasRelatedWork W2949725180 @default.
- W4313456443 hasRelatedWork W2950203649 @default.
- W4313456443 hasRelatedWork W2950465402 @default.
- W4313456443 hasRelatedWork W2953155228 @default.
- W4313456443 hasVolume "7" @default.
- W4313456443 isParatext "false" @default.
- W4313456443 isRetracted "false" @default.
- W4313456443 workType "article" @default.