3-hydroksyprolina i jej podstawione pochodne

• Autorzy: Hałajewska-Wosik A.

Warianty tytułu

EN

3-hydroxyproline and its substituted derivatives

• Języki publikacji: PL

Abstrakty

EN

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].

Słowa kluczowe

PL

kolagen; 3-hydroksyprolina; synteza; antybiotyki peptydowe; leki przeciwgrzybicze

EN

collagen; 3-hydroxyproline; synthesis; peptide antibiotics; antifungal drugs

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2010
• Tom: [Z] 64, 9-10
• Strony: 747--770
• Opis fizyczny: Bibliogr. 76 poz., schem.

Twórcy

autor

Hałajewska-Wosik A.

• Zakład Chemii Bioorganicznej, Wydział Farmaceutyczny, Uniwersytet Medyczny w Łodzi ul. Muszyńskiego 1, 90-151 Łódź,

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