Literature DB >> 28663711

GAP Peptide Synthesis via Design of New GAP Protecting Group: An Fmoc/tBu Synthesis of Thymopentin Free from Polymers, Chromatography and Recrystallization.

Cole W Seifert1, Armando Paniagua1, Gabrielle A White1, Lucy Cai2, Guigen Li1,3.   

Abstract

A novel method for Fmoc/tBu solution-phase peptide synthesis and the development of a new benzyl-type GAP protecting group is reported. This new GAP protecting group is utilized in place of a polymer support, facilitating C→N Fmoc peptide synthesis without chromatography, recrystallization, or polymer supports. The GAP group can be added and removed in high yield, and was used to synthesize over 1 gram of the immunostimulant, thymopentin, in high overall yield (83%) and purity (99%).

Entities:  

Keywords:  Amino Acids; GAP Chemistry; Peptides; Protecting Groups; Thymopentin

Year:  2016        PMID： 28663711      PMCID： PMC5486986          DOI： 10.1002/ejoc.201600026

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  19 in total

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Authors:  Albert Isidro-Llobet; Mercedes Alvarez; Fernando Albericio
Journal:  Chem Rev       Date:  2009-06       Impact factor: 60.622

2.  A mild removal of Fmoc group using sodium azide.

Authors:  Chun-Chi Chen; Basker Rajagopal; Xuan Yu Liu; Kuan Lin Chen; Yu-Chang Tyan; Fui Lin; Po-Chiao Lin
Journal:  Amino Acids       Date:  2013-12-05       Impact factor: 3.520

3.  Total synthesis of proanthocyanidin A1, A2, and their stereoisomers.

Authors:  Pradeep K Sharma; Leo J Romanczyk; Leelakrishna Kondaveti; Bollu Reddy; Jeeva Arumugasamy; Richard Lombardy; Yanni Gou; Hagen Schroeter
Journal:  Org Lett       Date:  2015-04-30       Impact factor: 6.005

Review 4.  N-Phosphonyl/phosphinyl imines and group-assisted purification (GAP) chemistry/technology.

Authors:  Guanghui An; Cole Seifert; Guigen Li
Journal:  Org Biomol Chem       Date:  2015-02-14       Impact factor: 3.876

5.  Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides.

Authors:  Tingting Fu; Hongwei Qiao; Zhimin Peng; Gaobo Hu; Xueji Wu; Yuxing Gao; Yufen Zhao
Journal:  Org Biomol Chem       Date:  2014-05-14       Impact factor: 3.876

6.  Total Synthesis of the Glycosylated Macrolide Antibiotic Fidaxomicin.

Authors:  Elias Kaufmann; Hiromu Hattori; Hideki Miyatake-Ondozabal; Karl Gademann
Journal:  Org Lett       Date:  2015-06-30       Impact factor: 6.005

7.  Regioselective formation of multiple disulfide bonds with the aid of postsynthetic S-tritylation.

Authors:  Masayoshi Mochizuki; Shugo Tsuda; Kyoko Tanimura; Yuji Nishiuchi
Journal:  Org Lett       Date:  2015-04-10       Impact factor: 6.005

8.  N-phosphinyl imine chemistry (I): design and synthesis of novel N-phosphinyl imines and their application to asymmetric aza-Henry reaction.

Authors:  Suresh Pindi; Parminder Kaur; Gaurav Shakya; Guigen Li
Journal:  Chem Biol Drug Des       Date:  2011-01       Impact factor: 2.817

9.  Asymmetric synthesis of α-amino-1,3-dithianes via chiral N-phosphonyl imine-based Umpolung reaction without using chromatography and recrystallization.

Authors:  Padmanabha V Kattamuri; Teng Ai; Suresh Pindi; Yinwei Sun; Peng Gu; Min Shi; Guigen Li
Journal:  J Org Chem       Date:  2011-03-15       Impact factor: 4.354

Review 10.  Chemical methods for peptide and protein production.

Authors:  Saranya Chandrudu; Pavla Simerska; Istvan Toth
Journal:  Molecules       Date:  2013-04-12       Impact factor: 4.411
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  5 in total

Review 1.  Greening the synthesis of peptide therapeutics: an industrial perspective.

Authors:  Vincent Martin; Peter H G Egelund; Henrik Johansson; Sebastian Thordal Le Quement; Felix Wojcik; Daniel Sejer Pedersen
Journal:  RSC Adv       Date:  2020-11-24       Impact factor: 4.036

2.  Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry.

Authors:  Hossein Rouh; Yao Tang; Sai Zhang; Ahmed I M Ali; Kazimierz Surowiec; Daniel Unruh; Guigen Li
Journal:  RSC Adv       Date:  2021-12-14       Impact factor: 4.036

3.  Aggregation-Induced Synthesis (AIS): Asymmetric Synthesis via Chiral Aggregates.

Authors:  Hossein Rouh; Yao Tang; Ting Xu; Qingkai Yuan; Sai Zhang; Jia-Yin Wang; Shengzhou Jin; Yu Wang; Junyi Pan; Hannah L Wood; James D McDonald; Guigen Li
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4.  Hypervalent Iodine (III) Catalyzed Regio- and Diastereoselective Aminochlorination of Tailored Electron Deficient Olefins via GAP Chemistry.

Authors:  Anis Ur Rahman; Nighat Zarshad; Peng Zhou; Weitao Yang; Guigen Li; Asad Ali
Journal:  Front Chem       Date:  2020-07-07       Impact factor: 5.221

5.  Multilayer 3D Chirality and Its Synthetic Assembly.

Authors:  Guanzhao Wu; Yangxue Liu; Zhen Yang; Nandakumar Katakam; Hossein Rouh; Sultan Ahmed; Daniel Unruh; Kazimierz Surowiec; Guigen Li
Journal:  Research (Wash D C)       Date:  2019-06-27
  5 in total

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