Literature DB >> 11950334

9-BBN: An amino acid protecting group for functionalization of amino acid side chains in organic solvents.

William H Dent1, W Randal Erickson, Stephen C Fields, Marshall H Parker, Eric G Tromiczak.   

Abstract

9-Borabicyclononane (9-BBN) has been utilized to protect functionalized amino acids for potential chemoselective side chain manipulation. The 9-BBN group imparts organic solubility to otherwise hydrophilic molecules and is tolerant of a wide range of reaction conditions. The high degree of solubility of these molecules in THF is particularly noteworthy. It is cleaved with either aqueous HCl or by exchange with ethylenediamine in methanol. [reaction: see text]

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Year:  2002        PMID: 11950334     DOI: 10.1021/ol017241b

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  Design, synthesis and brain uptake of LAT1-targeted amino acid prodrugs of dopamine.

Authors:  Lauri Peura; Kalle Malmioja; Kristiina Huttunen; Jukka Leppänen; Miia Hämäläinen; Markus M Forsberg; Mikko Gynther; Jarkko Rautio; Krista Laine
Journal:  Pharm Res       Date:  2013-10       Impact factor: 4.200

2.  A Divalent Protecting Group for Benzoxaboroles.

Authors:  Brett Vanveller; Matthew R Aronoff; Ronald T Raines
Journal:  RSC Adv       Date:  2013-11-28       Impact factor: 3.361

3.  Glycosylation modulates melanoma cell α2β1 and α3β1 integrin interactions with type IV collagen.

Authors:  Maciej J Stawikowski; Beatrix Aukszi; Roma Stawikowska; Mare Cudic; Gregg B Fields
Journal:  J Biol Chem       Date:  2014-06-23       Impact factor: 5.157

4.  Biosynthesis of HSAF, a tetramic acid-containing macrolactam from Lysobacter enzymogenes.

Authors:  Lili Lou; Guoliang Qian; Yunxuan Xie; Jiliang Hang; Haotong Chen; Kathia Zaleta-Rivera; Yaoyao Li; Yuemao Shen; Patrick H Dussault; Fengquan Liu; Liangcheng Du
Journal:  J Am Chem Soc       Date:  2010-12-20       Impact factor: 15.419

5.  Synthesis and solid-phase application of suitably protected gamma-hydroxyvaline building blocks.

Authors:  Mare Cudic; Frank Marí; Gregg B Fields
Journal:  J Org Chem       Date:  2007-06-21       Impact factor: 4.354

6.  Synthesis and Catalytic Activity of Amino Acids and Metallopeptides with Catalytically Active Metallocyclic Side Chains.

Authors:  Zhihui Zhong; Hao Yang; Chen Zhang; Jared C Lewis
Journal:  Organometallics       Date:  2012-10-18       Impact factor: 3.876

7.  Peptide-Based 2-Aminophenylamide Probes for Targeting Endogenous Class I Histone Deacetylase Complexes.

Authors:  Julian Seidel; Tobias Meisinger; Julia Sindlinger; Paulina Pieloch; Iris Finkemeier; Dirk Schwarzer
Journal:  Chembiochem       Date:  2019-09-26       Impact factor: 3.164

  7 in total

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