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Content available remote 3-hydroksyprolina i jej podstawione pochodne
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This article describes a biological activity of natural compounds containing 3-hydroxyproline and its substituted analogues. 3(S)-3-Hyp 3 was isolated from collagen in cattle's Achilles tendon in 1961 [4]. This amino acid in mammalian collagen is located only in the repeating sequence Gly-3-Hyp-4-Hyp [5] but its frequency is extremely low. Hydroxylation of prolyl residue to 3-Hyp 3 in collagen is catalyzed by prolyl-3-hydroxylase [6, 9]. It was proved that 4(R)-Hyp 2 greatly enhance the conformational stability of the collagen triple helix in contrast with 3(S)-Hyp 3, which destabilizing effect has been extensively investigated [7, 11, 12, 15]. The 3-hydroxyproline is also present in the invertebrates in the Fasciola hepatica [21]. The compounds 3 and/or 4 have been found in some peptide antibiotics: Telomycin 5, Plusbacin A3 6, Tripropeptins 7, Cyclothialidine 8 and in the antifungal drugs: Caspofungin 9 and Pneumocandin 10 [22–29]. Substituted derivatives of 3-hydroxyproline were also identified as components of biologically active compounds such as Polyoxypeptins A, B 12, Actinomycin 14, Paraherquamide 15 and Lactacystin 16 [30–36]. Due to the lack of a general synthetic methods for a stereoselective synthesis of substituted derivatives of 3-hydroxyproline some possibilities to obtain these compounds have been described in the second part of this paper [30–33, 36, 62, 65, 66, 68, 70, 73, 74, 76].
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