Literature DB >> 22489098

6'-Oxa Analogs of S-Adenosylhomocysteine.

Weikuan Li1, Wei Ye, Stewart W Schneller.   

Abstract

S-Adenosylmethionine (AdoMet) is a ubiquitous cofactor in biomethylations and, in that role, becomes S-adenosylhomocysteine (AdoHcy), which serves as a biofeedback inhibitor of the methylation process. In seeking to avail unexplored structural variations of AdoHcy for biological studies, its 6'-oxa analog and two corresponding carbocyclic nucleosides (based on aristeromycin and neplanocin) have been prepared via common convergent syntheses.

Entities:  

Year:  2012        PMID: 22489098      PMCID: PMC3320718          DOI: 10.1016/j.tet.2011.10.063

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  15 in total

Review 1.  S-adenosyl-L-homocysteine hydrolase as a target for antiviral chemotherapy.

Authors:  M S Wolfe; R T Borchardt
Journal:  J Med Chem       Date:  1991-05       Impact factor: 7.446

2.  John Montgomery's legacy: carbocyclic adenosine analogues as SAH hydrolase inhibitors with broad-spectrum antiviral activity.

Authors:  Erik De Clercq
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2005       Impact factor: 1.381

3.  Diastereoselective synthesis of quaternary alpha-amino acids from diketopiperazine templates.

Authors:  Stephen G Davies; A Christopher Garner; Jaqueline V A Ouzman; Paul M Roberts; Andrew D Smith; Emma J Snow; James E Thomson; Juan A Tamayo; Richard J Vickers
Journal:  Org Biomol Chem       Date:  2007-05-29       Impact factor: 3.876

Review 4.  Biological effects of inhibitors of S-adenosylhomocysteine hydrolase.

Authors:  P K Chiang
Journal:  Pharmacol Ther       Date:  1998-02       Impact factor: 12.310

5.  Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 1. Modification of the amino acid portion of S-adenosylhomocysteine.

Authors:  R T Borchardt; Y S Wu
Journal:  J Med Chem       Date:  1974-08       Impact factor: 7.446

6.  S-homoadenosyl-L-cysteine and S-homoadenosyl-L-homocysteine. Synthesis and binding studies of hon-hydrolyzed substrate analogues with S-adenosyl-L-homocysteine hydrolase.

Authors:  Robert W Miles; Lars P C Nielsen; Gregory J Ewing; Daniel Yin; Ronald T Borchardt; Morris J Robins
Journal:  J Org Chem       Date:  2002-11-15       Impact factor: 4.354

7.  Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS.

Authors:  Jong Hyun Cho; Dale L Bernard; Robert W Sidwell; Earl R Kern; Chung K Chu
Journal:  J Med Chem       Date:  2006-02-09       Impact factor: 7.446

8.  Structural basis for methyl transfer by a radical SAM enzyme.

Authors:  Amie K Boal; Tyler L Grove; Monica I McLaughlin; Neela H Yennawar; Squire J Booker; Amy C Rosenzweig
Journal:  Science       Date:  2011-04-28       Impact factor: 47.728

9.  Carbocyclic Sinefungin.

Authors:  Xueqiang Yin; Guoxia Zhao; Stewart W Schneller
Journal:  Tetrahedron Lett       Date:  2007-07-09       Impact factor: 2.415

10.  Preparative and stereoselective synthesis of the versatile intermediate for carbocyclic nucleosides: effects of the bulky protecting groups to enforce facial selectivity.

Authors:  Won Jun Choi; Hyung Ryong Moon; Hea Ok Kim; Byul Nae Yoo; Jeong A Lee; Dae Hong Shin; Lak Shin Jeong
Journal:  J Org Chem       Date:  2004-04-02       Impact factor: 4.354

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