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Stereoselective synthesis of (2S,3R)-alpha-hydroxy-beta-amino acids (AHBAs): valinoctin A, (2S,3R)-3-amino-2-hydroxydecanoic acid, and a fluorescent-labeled (2S,3R)-AHBA.
Deshmukh SC, Talukdar P. Deshmukh SC, et al. J Org Chem. 2014 Nov 21;79(22):11215-25. doi: 10.1021/jo501751u. Epub 2014 Oct 31. J Org Chem. 2014. PMID: 25308171
The utility of the methodology was demonstrated by the stereoselective synthesis of valinoctin A and (2S,3R)-3-amino-2-hydroxydecanoic acid ((2S,3R)-AHDA). Photophysical properties and cell permeability of a pyrene-labeled (2S,3R)-AHBA were also determined....
The utility of the methodology was demonstrated by the stereoselective synthesis of valinoctin A and (2S,3R)-3-amino-2-hydroxydecanoi …
Stereospecific synthesis of a novel farnesyl protein transferase inhibitor, valinoctin A and its analogues.
Tsuda M, Muraoka Y, Takeuchi T, Sekizawa R, Umezawa K. Tsuda M, et al. J Antibiot (Tokyo). 1996 Oct;49(10):1031-5. doi: 10.7164/antibiotics.49.1031. J Antibiot (Tokyo). 1996. PMID: 8968397 Free article.
(2S,3R)-3-Amino-2-hydroxyoctanoic acid was synthesized by Curtius rearrangement of an azide derivative of (S)-malic acid. Total syntheses of valinoctin A and its analogues were achieved by a coupling of (2S, 3R)-3-amino-2-hydroxyoctanoic acid moiety with L-valine or severa …
(2S,3R)-3-Amino-2-hydroxyoctanoic acid was synthesized by Curtius rearrangement of an azide derivative of (S)-malic acid. Total syntheses of …
Acylnitrene Route to Vicinal Amino Alcohols. Application to the Synthesis of (-)-Bestatin and Analogues.
Bergmeier SC, Stanchina DM. Bergmeier SC, et al. J Org Chem. 1999 Apr 16;64(8):2852-2859. doi: 10.1021/jo9823893. J Org Chem. 1999. PMID: 11674356
Bestatin, valinoctin A, and microginin are naturally occurring small peptides containing a nonproteinogenic alpha-hydroxy-beta-amino acid at the N-terminus of the peptide chain. ...
Bestatin, valinoctin A, and microginin are naturally occurring small peptides containing a nonproteinogenic alpha-hydroxy-beta-amino …
Isolation and synthesis of novel farnesyl protein transferase inhibitors, valinoctins A and B, from Streptomyces strain MJ858-NF3.
Sekizawa R, Iinuma H, Muraoka Y, Naganawa H, Kinoshita N, Nakamura H, Hamada M, Takeuchi T, Umezawa K. Sekizawa R, et al. J Nat Prod. 1996 Mar;59(3):232-6. doi: 10.1021/np960067t. J Nat Prod. 1996. PMID: 8882425
The tentative structures of these compounds were elucidated from NMR and mass spectra as dipeptides consisting of valine and a novel amino acyl moiety. Four possible isomers of valinoctin A were synthesized, and the protected derivative of the appropriate compound was crys …
The tentative structures of these compounds were elucidated from NMR and mass spectra as dipeptides consisting of valine and a novel amino a …