Reduced collagen cross links: the first synthesis of all the possible (2S,2′S)-stereoisomers of 5-hydroxylysinonorleucine and of 5,5′-dihydroxylysinonorleucine in enantiomerically pure form |
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| Institution: | 1. Institute of Biomaterial Science and Berlin-Brandenburg Centre for Regenerative Therapies, Helmholtz-Zentrum Geesthacht, 14513 Teltow, Germany;2. Institute of Chemistry, University of Potsdam, Potsdam-Golm, Germany;1. Department of Chemistry and the Tsinghua Center for Frontier Polymer Research, Tsinghua University, Beijing 100084, China;2. Beijing National Laboratory for Molecular Sciences, Key Laboratory of Polymer Chemistry and Physics of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China;3. Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Organic Solids, Laboratory of New Materials, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;1. Gedeon Richter Plc, H-1103 Budapest, Gyömrői út 19-21, Hungary;2. Department of Physical Chemistry, University of Debrecen, H-4032, Debrecen, Egyetem tér 1, Hungary;3. Department of Organic Chemistry, University of Debrecen, H-4032, Debrecen, Egyetem tér 1, Hungary;1. Department of Chemistry, AstraZeneca R&D Charnwood, Bakewell Road, Loughborough, Leicestershire LE11 5RH, UK;2. Department of Bioscience, AstraZeneca R&D Charnwood, Bakewell Road, Loughborough, Leicestershire LE11 5RH, UK;3. Emerging Innovations Unit, AstraZeneca R&D, Alderley Park, Cheshire SK10 4TF, UK;4. Respiratory, Inflammation & Autoimmunity iMed, AstraZeneca R&D, Molndal, Sweden;5. Argenta Discovery, Flex Meadow, Harlow CM19 5TR, UK;6. Argenta Discovery, Stoke Poges, Slough SL2 4SY, UK |
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| Abstract: | The paper reports the first enantioselective synthesis of all the possible collagen reduced cross links as described: (2S,2′S,5R)- and (2S,2′S,5S)-5-hydroxylysinonorleucine 3a and 3b, (2S,2′S,5R,5′R)-5,5′-dihydroxylysinonorleucine 4a, (2S,2′S,5R,5′S)-5,5′-dihydroxylysinonorleucine 4b and (2S,2′S,5S,5′S)-5,5′-dihydroxylysinonorleucine 4c. The Williams’ glycine template methodology was used both for the introduction of a stereogenic at the α-position and for an easy protection of the amino acidic functionalities during the synthesis of the dimeric amino acids. |
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