Literature DB >> 22697488

A new Oxyma derivative for nonracemizable amide-forming reactions in water.

Qinghui Wang1, Yong Wang, Michio Kurosu.   

Abstract

An Oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (2), displayed remarkable physicochemical properties as a peptide-coupling additive for peptide-forming reactions in water. Short peptides to oligopeptides could be synthesized by using 2, EDCI, and NaHCO(3) in water without measurable racemization. Significantly, a simple basic and acidic aqueous workup procedure can remove all reagents utilized in the reactions to afford only coupling products in consistently excellent yields.

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Year:  2012        PMID： 22697488      PMCID： PMC3431018          DOI： 10.1021/ol3013556

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


  6 in total

Review 1.  Large-scale manufacture of peptide therapeutics by chemical synthesis.

Authors:  Brian L Bray
Journal:  Nat Rev Drug Discov       Date:  2003-07       Impact factor: 84.694

2.  Oxyma: an efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion.

Authors:  Ramon Subirós-Funosas; Rafel Prohens; Rafael Barbas; Ayman El-Faham; Fernando Albericio
Journal:  Chemistry       Date:  2009-09-21       Impact factor: 5.236

Review 3.  Peptide coupling reagents, more than a letter soup.

Authors:  Ayman El-Faham; Fernando Albericio
Journal:  Chem Rev       Date:  2011-08-26       Impact factor: 60.622

Review 4.  Advances in the chemistry of carbodiimides.

Authors:  F Kurzer; K Douraghi-Zadeh
Journal:  Chem Rev       Date:  1967-04       Impact factor: 60.622

5.  Solid-phase peptide synthesis in water using microwave-assisted heating.

Authors:  Athanassios S Galanis; Fernando Albericio; Morten Grøtli
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

6.  Solid phase peptide synthesis in water VI: evaluation of water-soluble coupling reagents for solid phase peptide synthesis in aqueous media.

Authors:  Keiko Hojo; Mitsuko Maeda; Naoko Tanakamaru; Kayo Mochida; Koichi Kawasaki
Journal:  Protein Pept Lett       Date:  2006       Impact factor: 1.890
  6 in total
  15 in total

1.  Substrate Tolerance of Bacterial Glycosyltransferase MurG: Novel Fluorescence-Based Assays.

Authors:  Katsuhiko Mitachi; Hyun Gi Yun; Cody D Gillman; Karolina Skorupinska-Tudek; Ewa Swiezewska; William M Clemons; Michio Kurosu
Journal:  ACS Infect Dis       Date:  2019-12-11       Impact factor: 5.084

2.  Improved synthesis of capuramycin and its analogues.

Authors:  Yong Wang; Shajila Siricilla; Bilal A Aleiwi; Michio Kurosu
Journal:  Chemistry       Date:  2013-09-06       Impact factor: 5.236

3.  DPAGT1 Inhibitors of Capuramycin Analogues and Their Antimigratory Activities of Solid Tumors.

Authors:  Katsuhiko Mitachi; Rita G Kansal; Kirk E Hevener; Cody D Gillman; Syed M Hussain; Hyun Gi Yun; Gustavo A Miranda-Carboni; Evan S Glazer; William M Clemons; Michio Kurosu
Journal:  J Med Chem       Date:  2020-09-18       Impact factor: 7.446

4.  Selective esterifications of primary alcohols in a water-containing solvent.

Authors:  Yong Wang; Bilal A Aleiwi; Qinghui Wang; Michio Kurosu
Journal:  Org Lett       Date:  2012-08-31       Impact factor: 6.005

5.  Mild and convenient N-formylation protocol in water-containing solvents.

Authors:  Bilal A Aleiwi; Katsuhiko Mitachi; Michio Kurosu
Journal:  Tetrahedron Lett       Date:  2013-04-17       Impact factor: 2.415

6.  A New Combination of a Pleuromutilin Derivative and Doxycycline for Treatment of Multidrug-Resistant Acinetobacter baumannii.

Authors:  Shajila Siricilla; Katsuhiko Mitachi; Junshu Yang; Shakiba Eslamimehr; Maddie R Lemieux; Bernd Meibohm; Yinduo Ji; Michio Kurosu
Journal:  J Med Chem       Date:  2017-03-22       Impact factor: 7.446

7.  Oxyma-based phosphates for racemization-free peptide segment couplings.

Authors:  Katsuhiko Mitachi; Yuki E Kurosu; Brandon T Hazlett; Michio Kurosu
Journal:  J Pept Sci       Date:  2016-03       Impact factor: 1.905

8.  Stereocontrolled Total Synthesis of Muraymycin D1 Having a Dual Mode of Action against Mycobacterium tuberculosis.

Authors:  Katsuhiko Mitachi; Bilal A Aleiwi; Christopher M Schneider; Shajila Siricilla; Michio Kurosu
Journal:  J Am Chem Soc       Date:  2016-09-26       Impact factor: 15.419

9.  Structure determination of lipopeptides from Mycobacterium avium subspecies paratuberculosis and identification of antigenic lipopeptide probes.

Authors:  Katsuhiko Mitachi; Lekh Nath Sharma Gautam; Jeffrey H Rice; Keiko Eda; Ashutosh Wadhwa; Eiichi Momotani; Joseph P Hlopak; Shigetoshi Eda; Michio Kurosu
Journal:  Anal Biochem       Date:  2016-04-22       Impact factor: 3.365

10.  One-pot protection-glycosylation reactions for synthesis of lipid II analogues.

Authors:  Katsuhiko Mitachi; Priya Mohan; Shajila Siricilla; Michio Kurosu
Journal:  Chemistry       Date:  2014-03-12       Impact factor: 5.236
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