1377320-83-6Relevant articles and documents
syn-selective additions to Garner aldehyde: Synthesis of a potent glucosylceramide synthase inhibitor
Husain, Arifa,Ganem, Bruce
, p. 8621 - 8623 (2002)
Highly syn-selective additions of aryl Grignard reagents to Garner aldehyde 5 are reported, making possible a practical, asymmetric synthesis of the potent glucosylceramide synthase inhibitor 3.
Total Synthesis of Glycosylated Human Interferon-γ
Ashhurst, Anneliese S.,Dowman, Luke J.,Fairbanks, Antony J.,Kwan, Ann,Larance, Mark,Li, Henry Y.,Payne, Richard J.,Wang, Xiaoyi,Watson, Emma E.
supporting information, p. 6863 - 6867 (2020/09/15)
Interferon-γ(IFN-γ) is a glycoprotein that is responsible for orchestrating numerous critical immune induction and modulation processes and is used clinically for the treatment of a number of diseases. Herein, we describe the total chemical synthesis of homogeneously glycosylated variants of human IFN-γusing a tandem diselenide-selenoester ligation-deselenization strategy in the C- to N-terminal direction. The synthetic glycoproteins were successfully folded, and the structures and antiviral functions were assessed.
Synthetic Studies Toward the Skyllamycins: Total Synthesis and Generation of Simplified Analogues
Giltrap, Andrew M.,Haeckl, F. P. Jake,Kurita, Kenji L.,Linington, Roger G.,Payne, Richard J.
, p. 7250 - 7270 (2018/06/01)
Herein, we report our synthetic studies toward the skyllamycins, a highly modified class of nonribosomal peptide natural products which contain a number of interesting structural features, including the extremely rare α-OH-glycine residue. Before embarking on the synthesis of the natural products, we prepared four structurally simpler analogues. Access to both the analogues and the natural products first required the synthesis of a number of nonproteinogenic amino acids, including three β-OH amino acids that were accessed from the convenient chiral precursor Garner's aldehyde. Following the preparation of the suitably protected nonproteinogenic amino acids, the skyllamycin analogues were assembled using a solid-phase synthetic route followed by a final stage solution-phase cyclization reaction. To access the natural products (skyllamycins A-C) the synthetic route used for the analogues was modified. Specifically, linear peptide precursors containing a C-terminal amide were synthesized via solid-phase peptide synthesis. After cleavage from the resin the N-terminal serine residue was oxidatively cleaved to a glyoxyamide moiety. The target natural products, skyllamycins A-C, were successfully prepared via a final step cyclization with concomitant formation of the unusual α-OH-glycine residue. Purification and spectroscopic comparison to the authentic isolated material confirmed the identity of the synthetic natural products.
Total Synthesis of Skyllamycins A–C
Giltrap, Andrew M.,Haeckl, F. P. Jake,Kurita, Kenji L.,Linington, Roger G.,Payne, Richard J.
supporting information, p. 15046 - 15049 (2017/10/31)
The skyllamycins are a family of highly functionalized non-ribosomal cyclic depsipeptide natural products which contain the extremely rare α-OH-glycine functionality. Herein the first total synthesis of skyllamycins A–C is reported, together with the biofilm inhibitory activity of the natural products. Linear peptide precursors for each natural product were prepared through an efficient solid-phase route incorporating a number of synthetic modified amino acids. A novel macrocyclization step between a C-terminal amide and an N-terminal glyoxylamide moiety served as a key transformation to install the unique α-OH-glycine unit and generate the natural products in the final step of the synthesis.
Synthesis of β-Thiol Phenylalanine for Applications in One-Pot Ligation-Desulfurization Chemistry
Malins, Lara R.,Giltrap, Andrew M.,Dowman, Luke J.,Payne, Richard J.
supporting information, p. 2070 - 2073 (2015/05/13)
(Chemical Equation Presented) The efficient synthesis of a β-thiol phenylalanine derivative is described starting from Garner's aldehyde. The utility of this amino acid in peptide ligation-desulfurization chemistry is described, including the trifluoroethanethiol (TFET)-promoted one-pot assembly of the 62 residue peptide hormone augurin.
A concise and simple synthesis of 1-hydroxy-phenethylamine derivatives: Formal synthesis of naturally occurring norephedrine, virolin and 3-hydroxy-2-phosphonylmethoxypropyl adenine
Saha,Chakraborty,Roy
, p. 837 - 846 (2014/07/07)
A concise and simple synthesis of 1-hydroxy-phenethylamine derivatives has been achieved following classical organic transformations using commercially available chiral pools. The said derivatives were explored for the synthesis of naturally occurring bio-active small molecules. Formal synthesis of norephedrine, virolin and 3-hydroxy-2-phosphonylmethoxypropyl adenine has been demonstrated.
Asymmetric synthesis of cis-2,5-disubstituted pyrrolidine, the core scaffold of β3-AR agonists
Xu, Feng,Chung, John Y. L.,Moore, Jeffery C.,Liu, Zhuqing,Yoshikawa, Naoki,Hoerrner, R. Scott,Lee, Jaemoon,Royzen, Maksim,Cleator, Ed,Gibson, Andrew G.,Dunn, Robert,Maloney, Kevin M.,Alam, Mahbub,Goodyear, Adrian,Lynch, Joseph,Yasuda, Nobuyashi,Devine, Paul N.
supporting information, p. 1342 - 1345 (2013/04/24)
A practical, enantioselective synthesis of cis-2,5-disubstituted pyrrolidine is described. Application of an enzymatic DKR reduction of a keto ester, which is easily accessed through a novel intramolecular N→C benzoyl migration, yields syn-1,2-amino alcoh
Synthesis and utility of β-selenol-phenylalanine for native chemical ligation-deselenization chemistry
Malins, Lara R.,Payne, Richard J.
supporting information; experimental part, p. 3142 - 3145 (2012/10/07)
An efficient synthetic route to a suitably protected β-selenol- phenylalanine derivative from commercially available Garner's aldehyde is described. The incorporation of this building block into peptides and its application in native chemical ligation reactions with peptide thioesters are demonstrated. Ligation products were chemoselectively deselenized (including in the presence of unprotected cysteine residues) to provide native peptides.
Asymmetric synthesis of a dopamine D1 agonist, dihydrexidine from d-serine
Malhotra, Rajesh,Ghosh, Amit,Ghosh, Rajib,Chakrabarti, Sagar,Dutta, Swarup,Dey, Tushar K.,Roy, Subho,Basu, Sourav,Hajra, Saumen
body text, p. 1522 - 1529 (2011/12/14)
A scalable asymmetric synthesis of trans-2-amino-6,7-dimethoxy-1- phenyltetralin 2 and its N-nosyl derivative 12 have been achieved from Garner aldehyde derived from easily available d-serine using a stereoselective PhMgBr addition, Wittig reaction and TF
Preparation of enantiomerically pure 2-(1′-aminomethyl)furan derivatives and synthesis of an unnatural polyhydroxylated piperidine
Cong, Xin,Liu, Ke-Gang,Liao, Qing-Jiang,Yao, Zhu-Jun
, p. 8567 - 8571 (2007/10/03)
Zinc-mediated propargylation of α-acylaminoaldehydes, and subsequent oxidative isomerization followed by Ag(I)-catalyzed cycloisomerization conveniently provides a new enantioselective route to the corresponding 2-aminoalkylfurans. One of these furans was
