106391-85-9Relevant articles and documents
Diastereoselective synthesis of 3-amino-1,2-diols by reductive alkylation of 2,3-dialkoxynitriles
Hutin, Pierre,Larchevêque, Marc
, p. 2369 - 2372 (2000)
The addition of Grignard reagents to acetonide protected syn 2,3- dihydroxynitriles, followed by reduction of the resulting magnesioimines, affords all syn 1,3-disubstituted 3-amino-1,2-diols in high enantiomeric purities. (C) 2000 Published by Elsevier Science Ltd.
Synthesis of photoactive analogues of a cystine knot trypsin inhibitor protein
Durek, Thomas,Zhang, Junliang,He, Chuan,Kent, Stephen B. H.
, p. 5497 - 5500 (2007)
We describe the preparation of a recently described photoactive amino acid analogue (photoMethionine) by two novel synthetic routes, one of which is flexible and enantiospecific, and the site-specific chemical incorporation of photoMethionine into a defined and functionally active protein using a combination of solid-phase peptide synthesis and modern chemical ligation methodology. Site-specific labeling of proteins with this amino acid analogue through chemical synthesis provides valuable probes for photoaffinity cross-linking studies.
Conformational properties of ascydiacyclamide analogues with cyclic α-amino acids instead of oxazoline residues
Asano, Akiko,Numata, Shohei,Yamada, Takeshi,Minoura, Katsuhiko,Doi, Mitsunobu
, p. 6554 - 6562 (2017)
Ascidiacyclamide [ASC, cyclo(-Ile-oxazoline-D-Val-thiazole-)2] is a cyclic octapeptide isolated from tunicates. We designed ASC analogues [cyclo(-Ile-Xxx-D-Val-thiazole-)2] in which Pro or a homologue was substituted for oxazoline: [Pro]ASC (Xxx: proline), [Aze]ASC (Xxx: (S)-Azetidine-2-carboxylic acid), [Pip]ASC (Xxx: (S)-Piperidine-2-carboxylic acid) and [ΔPro]ASC (Xxx: (S)-3-pyrroline-2-carboxylic acid) to explore their potential to serve as substitutes for the oxazoline ring. The conformations of these analogues were examined using X-ray diffraction, 1H NMR and CD spectroscopy. In both the crystal and solution states, the conformations of [Pro]ASC, [Aze]ASC and [ΔPro]ASC were novel square structures having two trans imide bonds and stabilized by two intramolecular hydrogen bonds. The crystal structure of [Pip]ASC was a folded conformation with cis and trans imide bonds. Three isomers (cc, ct and tt) were present in a solution of [Pip]ASC. From crystal structures, the degree of puckering in the side chains of Pro and its homologues was estimated to be in the order Pip > Pro > Aze > ΔPro. [Pro]ASC and [Pip]ASC showed strong cytotoxicity, but [Aze]ASC and [ΔPro]ASC showed no cytotoxicity. Among the four analogues, there is consistency between the prolyl ring puckering and cytotoxicity, but not between the peptide backbone structure and cytotoxicity.
TRPV3 Modulators
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Page/Page column 50, (2012/10/08)
Disclosed herein are modulators of TRPV3 of formula (I) wherein X1, X2, R1, R2, Rx, and n are as defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also presented.