Academic Journal
N-Acetyl-l-phenylalanine Racemization during TBTU Amidation: An In-Depth Study for the Synthesis of Anti-Inflammatory 2-(N-Acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA)
| العنوان: | N-Acetyl-l-phenylalanine Racemization during TBTU Amidation: An In-Depth Study for the Synthesis of Anti-Inflammatory 2-(N-Acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA) |
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| المؤلفون: | Sturabotti, Elisa, Vetica, Fabrizio, Toscano, Giorgia, Calcaterra, Andrea, Martinelli, Andrea, Migneco, Luisa Maria, Leonelli, Francesca |
| المساهمون: | Sturabotti, Elisa, Vetica, Fabrizio, Toscano, Giorgia, Calcaterra, Andrea, Martinelli, Andrea, Migneco, Luisa Maria, Leonelli, Francesca |
| بيانات النشر: | MDPI |
| سنة النشر: | 2023 |
| المجموعة: | Sapienza Università di Roma: CINECA IRIS |
| مصطلحات موضوعية: | racemization, N-acetyl amino acid, coupling, TBTU, pyridine |
| الوصف: | A thorough study on the amidation conditions of N-acetyl-l-phenylalanine using TBTU and various bases is reported for the synthesis of 2-(N-acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA), a promising drug for the treatment of joints diseases. TBTU-mediated diastereoselective amidation reaction with 1,3,4,6-tetra-O-acetyl-β-d-glucosamine always gave racemization of N-acetyl-l-phenylalanine. The stereochemical retention under amidation conditions was studied in detail in the presence of difference bases and via other control experiments, evidencing the possibility to reduce racemization using pyridine as base. |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| Relation: | info:eu-repo/semantics/altIdentifier/pmid/36677671; info:eu-repo/semantics/altIdentifier/wos/WOS:000918673200001; volume:28; issue:2; numberofpages:12; journal:MOLECULES; https://hdl.handle.net/11573/1664403; info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85146749903 |
| DOI: | 10.3390/molecules28020581 |
| الاتاحة: | https://hdl.handle.net/11573/1664403 https://doi.org/10.3390/molecules28020581 |
| Rights: | info:eu-repo/semantics/openAccess |
| رقم الانضمام: | edsbas.8AF7BBAC |
| قاعدة البيانات: | BASE |
| DOI: | 10.3390/molecules28020581 |
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