Literature DB >> 31920214

Key side products due to reactivity of dimethylmaleoyl moiety as amine protective group.

Mijoon Lee1, Dusan Hesek1, Bruce C Noll1, Shahriar Mobashery1.   

Abstract

Dimethylmaleoyl (DMM) moiety has become an important amine protective group in sugar chemistry. We disclose herein that DMM-containing d-glucosamine analogues, because of their electrophilic nature, are prone to reactions with strong nucleophiles, such as hydrazine, resulting in a set of undesired side products that are difficult to detect, yet proved to be problematic for organic synthesis.

Entities:  

Keywords:  amine protective group; carbohydrate; dimethylmaleoyl; glucosamine; peptidoglycan

Year:  2009        PMID： 31920214      PMCID： PMC6952067          DOI： 10.2478/s11696-009-0048-0

Source DB:  PubMed          Journal:  Chem Zvesti        ISSN： 0366-6352            Impact factor:   2.097


  8 in total

1.  Synthesis of chitotetraose and chitohexaose based on dimethylmaleoyl protection.

Authors:  M R Aly; E S Ibrahim; E S El Ashry; R R Schmidt
Journal:  Carbohydr Res       Date:  2001-03-22       Impact factor: 2.104

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Activation for catalysis of penicillin-binding protein 2a from methicillin-resistant Staphylococcus aureus by bacterial cell wall.

Authors:  Cosimo Fuda; Dusan Hesek; Mijoon Lee; Ken-ichiro Morio; Thomas Nowak; Shahriar Mobashery
Journal:  J Am Chem Soc       Date:  2005-02-23       Impact factor: 15.419

4.  Three-dimensional structure of the bacterial cell wall peptidoglycan.

Authors:  Samy O Meroueh; Krisztina Z Bencze; Dusan Hesek; Mijoon Lee; Jed F Fisher; Timothy L Stemmler; Shahriar Mobashery
Journal:  Proc Natl Acad Sci U S A       Date:  2006-03-09       Impact factor: 11.205

5.  Synthesis of a fragment of bacterial cell wall.

Authors:  Dusan Hesek; Mijoon Lee; Ken-ichiro Morio; Shahriar Mobashery
Journal:  J Org Chem       Date:  2004-03-19       Impact factor: 4.354

6.  Synthetic peptidoglycan substrates for penicillin-binding protein 5 of Gram-negative bacteria.

Authors:  Dusan Hesek; Maxim Suvorov; Ken-Ichiro Morio; Mijoon Lee; Stephen Brown; Sergei B Vakulenko; Shahriar Mobashery
Journal:  J Org Chem       Date:  2004-02-06       Impact factor: 4.354

7.  Elucidation of the molecular recognition of bacterial cell wall by modular pneumococcal phage endolysin CPL-1.

Authors:  Inmaculada Pérez-Dorado; Nuria E Campillo; Begoña Monterroso; Dusan Hesek; Mijoon Lee; Juan A Páez; Pedro García; Martín Martínez-Ripoll; José L García; Shahriar Mobashery; Margarita Menéndez; Juan A Hermoso
Journal:  J Biol Chem       Date:  2007-06-19       Impact factor: 5.157

8.  Structural insights into the bactericidal mechanism of human peptidoglycan recognition proteins.

Authors:  Sangwoo Cho; Qian Wang; Chittoor P Swaminathan; Dusan Hesek; Mijoon Lee; Geert-Jan Boons; Shahriar Mobashery; Roy A Mariuzza
Journal:  Proc Natl Acad Sci U S A       Date:  2007-05-14       Impact factor: 11.205
  8 in total

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