Asymmetric Syntheses of (2R,3S)-3-Hydroxyproline and (2S,3S)-3-Hydroxyproline
نویسندگان
چکیده
منابع مشابه
Studies on 3-methoxyproline and 3-hydroxyproline.
The cis and trans racemates of synthetic 3-hydroxyproline and of synthetic 3-methoxyproline were interconverted by an epimerization reaction at carbon atom 2. The interconversions are proof of the diastereomeric nature of the synthetic isomers. Assignments of cis and trans configuration were made from nuclear magnetic resonance studies. Synthetic cisand trans-3-hydroxy-DL-proline were partially...
متن کامل3-Hydroxyproline content of normal urine.
Values for total 3-hydroxyproline and 4-hydroxyproline were obtained from 24-h urine specimens of 18 healthy human subjects of both sexes, whose ages ranged from the first to the sixth decade in age. Urinary 3-hydroxyproline levels, not earlier described to our knowledge, were determined by an isotope-dilution method requiring considerable purification and utilizing the amino acid analyzer for ...
متن کاملEffect of 3-hydroxyproline residues on collagen stability.
Collagen is an integral part of many types of connective tissue in animals, especially skin, bones, cartilage, and basement membranes. A fibrous protein, collagen has a triple-helical structure, which is comprised of strands with a repeating Xaa-Yaa-Gly sequence. l-Proline (Pro) and 4(R)-hydroxy-l-proline (4-Hyp) residues occur most often in the Xaa and Yaa positions. The 4-Hyp residue is known...
متن کاملContiguous hydroxyproline residues direct hydroxyproline arabinosylation in Nicotiana tabacum.
Hydroxyproline (Hyp) O-glycosylation characterizes the hydroxyproline-rich glycoprotein (HRGP) superfamily of the plant extracellular matrix. Hyp glycosylation occurs in two modes: Arabinosylation adds short oligoarabinosides (Hyp-arabinosides) while galactosylation leads to the addition of larger arabinogalactan polysaccharides (Hyp-polysaccharides). We hypothesize that sequence-dependent glyc...
متن کاملStereoisomers of hydroxyproline.
Hydroxy-L-proline was first isolated by Fischer in 1902 from a hydrolysate of gelatin (l).l The synthesis and determination of the structure were reported by Leuchs and coworkers (5--g), and, in 1919, the separation of the two racemic stereoisomers and the resolution of each racemate through mixtures of quinine with the corresponding N-phenylisocyanate derivatives were accomplished (5). In the ...
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2018
ISSN: 1523-7060,1523-7052
DOI: 10.1021/acs.orglett.8b01736