{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T22:38:07Z","timestamp":1791412687929,"version":"4.3.3"},"reference-count":30,"publisher":"Beilstein Institut","license":[{"start":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T00:00:00Z","timestamp":1788393600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T00:00:00Z","timestamp":1788393600000},"content-version":"am","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T00:00:00Z","timestamp":1788393600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"DOI":"10.13039\/100018329","name":"AiF Projekt","doi-asserted-by":"publisher","award":["KK5064604SK4"],"award-info":[{"award-number":["KK5064604SK4"]}],"id":[{"id":"10.13039\/100018329","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["316213987, SFB 1278 PolyTarget (Project No. A04)"],"award-info":[{"award-number":["316213987, SFB 1278 PolyTarget (Project No. A04)"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Beilstein J. Org. Chem."],"accepted":{"date-parts":[[2026,8,18]]},"abstract":"<jats:p>\n                    3-\n                    <jats:italic>O<\/jats:italic>\n                    -Acetyl-11-keto-\u03b2-boswellic acid (AKBA) is an anti-inflammatory constituent of frankincense. Its potency is attributed to its ability to interact with enzymes in the inflammation cascade, such as lipoxygenase and cyclooxygenase, to decrease formation of pro-inflammatory products while increasing the production of pro-resolving mediators. However, the availability of AKBA in vivo may be limited by factors such as poor solubility and protein binding in serum. A prodrug approach, wherein AKBA is conjugated to amino acids through its carboxylate moiety, could be a suitable way to improve solubility and half-life in blood while maintaining anti-inflammatory efficacy. In this study, we describe a robust protocol for the preparation of high-purity amino acid-AKBA conjugates, exemplified by synthesis of the \u029f-alaninate derivative AKBA-Ala. The alanine conjugate was characterized by NMR spectroscopy, ESI-MS, HPLC, and X-ray crystallography, representing the first reported solid-state structure of an amino acid-AKBA conjugate. In comparison to AKBA, biological investigations of AKBA-Ala demonstrated a reduced inhibition (40% weaker at 10 \u00b5M) of 5-lipoxygenase (5-LOX) product formation in human neutrophils, but slightly enhanced production (120% higher at 10 \u00b5M) of specialized pro-resolving mediators (SPM) in human M2 macrophages. Overall, the anti-inflammatory potency of AKBA-Ala remains comparable to that of AKBA.\n                  <\/jats:p>","DOI":"10.3762\/bjoc.22.99","type":"journal-article","created":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T09:38:58Z","timestamp":1788428338000},"page":"1229-1236","source":"Crossref","is-referenced-by-count":1,"title":["Molecular structure of 3-\n                    <i>O<\/i>\n                    -acetyl-11-keto-\u03b2-boswellic acid and its \u029f-alanine conjugate (AKBA-Ala) and their impact on lipoxygenases"],"prefix":"10.3762","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0009-0002-4787-2757","authenticated-orcid":false,"given":"Jan 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