Collagen mimics

Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Tripeptides – e.g. – tripeptide thyroliberin – etc.

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Details

530329, 530345, 530356, A61K 3806, C07K 1700

Patent

active

059731125

ABSTRACT:
A novel collagen mimic comprising a tripeptide unit having the formula (XaaFlpGly).sub.n, where Flp is 4(R)-fluoro-L-proline, is disclosed. The collagen mimic has increased stability relative to the collagen-related triple helices (ProProGly).sub.n and (ProHypGly).sub.n.

REFERENCES:
Gottlieb et al. Biochemistry, vol. 4, No. 11 pp. 2507-2513, 1965.
Eberhardt et al. Journal of the American Chemical Society, vol. 118, No. 49, pp. 12261-12266, 1996.
Panasik, Jr., et al, International Journal of Peptide & Protein Research, vol. 44, pp. 262-269, 1994.
Bella, Jordi, et al., "Crystal and Molecular Structure of a Collagen-Like Peptide at 1.9 .ANG. Resolution," Science, 266:75-81 (Oct. 7, 1994).
Eberhardt, Eric S., et al., "Inductive Effects on the Energentics of Prolyl Peptide Bond Isomerization: Implications for Collagen Folding and Stability," Journal of the American Chemical Society, 118(49):12261-12266 (1996).
Gottlieb, A. Arthur, et al., "Incorporation of cis-and trans-4-Fluoro-L-prolines into Proteins and Hydroxylation of the trans Isomer During Collagen Biosynthesis," Biochemistry, 4(11)2507-2513 (Nov. 1965).
Panasik, Nicholas, Jr., et al., "Inductive effects on the structure of proline residues," International Journal of Peptide & Protein Research, 44:262-269 (1994).
Sakakibara, Shumpei, et al., "Synthesis of (Pro-Hyp-Gly).sub.n of defined molecular weights Evidence for the stabilization of collagen triple helix by hydroxypyroline," Biochimica et Biophysica Acta, 303:198-202 (1973).

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