Literature DB >> 14723531

An efficient synthesis of a probe for protein function: 2,3-diaminopropionic acid with orthogonal protecting groups.

Ethan A Englund1, Hosahudya N Gopi, Daniel H Appella.   

Abstract

[reaction: see text] An efficient and cost-effective synthesis of N(alpha)-Boc2-N(beta)-Cbz-2,3-diaminopropionic acid is reported. The synthesis starts from commercially available N(alpha)-Boc-Asp(OBn)-OH and employs a Curtius rearrangement to establish the beta-nitrogen. Proper protection of the alpha-nitrogen is essential for the success of the Curtius rearrangement.

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Year:  2004        PMID: 14723531     DOI: 10.1021/ol0361599

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


  3 in total

Review 1.  The Curtius rearrangement: mechanistic insight and recent applications in natural product syntheses.

Authors:  Arun K Ghosh; Anindya Sarkar; Margherita Brindisi
Journal:  Org Biomol Chem       Date:  2018-02-26       Impact factor: 3.876

2.  Synthesis and in vitro and in vivo characterization of highly β1-selective β-adrenoceptor partial agonists.

Authors:  Shailesh N Mistry; Jillian G Baker; Peter M Fischer; Stephen J Hill; Sheila M Gardiner; Barrie Kellam
Journal:  J Med Chem       Date:  2013-05-10       Impact factor: 7.446

3.  2,3-Diaminopropanols Obtained from d-Serine as Intermediates in the Synthesis of Protected 2,3-l-Diaminopropanoic Acid (l-Dap) Methyl Esters.

Authors:  Andrea Temperini; Donatella Aiello; Fabio Mazzotti; Constantinos M Athanassopoulos; Pierantonio De Luca; Carlo Siciliano
Journal:  Molecules       Date:  2020-03-13       Impact factor: 4.411

  3 in total

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