دورية أكاديمية
Site-Selective Incorporation of a Functional Group into Lys175 in the Vicinity of the Active Site of Chymotrypsin by Using Peptidyl α-Aminoalkylphosphonate Diphenyl Ester-Derivatives
| العنوان: | Site-Selective Incorporation of a Functional Group into Lys175 in the Vicinity of the Active Site of Chymotrypsin by Using Peptidyl α-Aminoalkylphosphonate Diphenyl Ester-Derivatives |
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| المؤلفون: | Shin Ono, Masato Koga, Yuya Arimura, Takahiro Hatakeyama, Mai Kobayashi, Jun-ichi Sagara, Takahiko Nakai, Yoshikazu Horino, Hirofumi Kuroda, Hiroshi Oyama, Kazunari Arima |
| المصدر: | Molecules, Vol 28, Iss 7, p 3150 (2023) |
| بيانات النشر: | MDPI AG, 2023. |
| سنة النشر: | 2023 |
| المجموعة: | LCC:Organic chemistry |
| مصطلحات موضوعية: | chymotrypsin, dansyl group, diphenyl α-aminoalkylphosphonate, site-selective chemical modification, Organic chemistry, QD241-441 |
| الوصف: | We previously reported that Lys175 in the region of the active site of chymotrypsin (Csin) could be site-selectively modified by using an N-hydroxy succinimide (NHS) ester of the peptidyl derivative containing 1-amino-2-ethylphenylphosphonate diphenyl ester [NHS-Suc-Ala-Ala-PheP(OPh)2]. In this study, the Lys175-selective modification method was expanded to incorporate functional groups into Lys 175 in Csin. Two types of peptidyl phosphonate derivatives with the dansyl group (Dan) as a functional molecule, Dan-β-Ala-[Asp(NHS) or Glu(NHS)]-Ala-Ala-(R)-PheP(OPh)2 (DanD and DanE, respectively), were synthesized, and their action was evaluated when modifying Lys175 in Csin. Ion-exchange chromatography (IEC), fluorescence spectroscopy, and LC-MS/MS were used to analyze the products from the reaction of Csin with DanD or DanE. By IEC and LC-MS/MS, the results showed that DanE reacted with Csin more effectively than DanD to produce the modified Csin (DanMCsin) bearing Dan at Lys175. DanMCsin exhibited an enzymatic activity corresponding to 1/120 of Csin against Suc-Ala-Ala-Phe-pNA. In addition, an effect of Lys175 modification on the access of the proteinaceous Bowman–Birk inhibitor to the active site of DanMCsin was investigated. In conclusion, by using a peptidyl derivative containing 1-amino-2-ethylphenylphosphonate diphenyl ester, we demonstrated that a functional group could be incorporated into Lys175 in Csin. |
| نوع الوثيقة: | article |
| وصف الملف: | electronic resource |
| اللغة: | English |
| تدمد: | 28073150 1420-3049 |
| العلاقة: | https://www.mdpi.com/1420-3049/28/7/3150Test; https://doaj.org/toc/1420-3049Test |
| DOI: | 10.3390/molecules28073150 |
| الوصول الحر: | https://doaj.org/article/3553faefa8914ce1b193d91d3b2181a2Test |
| رقم الانضمام: | edsdoj.3553faefa8914ce1b193d91d3b2181a2 |
| قاعدة البيانات: | Directory of Open Access Journals |
Full Text Finder | تدمد: | 28073150 14203049 |
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| DOI: | 10.3390/molecules28073150 |