Derivatives and Peptides of 4–hydroxyproline: A Compendium

Adams, Elijah

doi:10.1111/j.1399-3011.1977.tb03493.x

Cited by 4 publications

References 98 publications

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Heterotrimeric collagen peptides containing functional epitopes. Synthesis of single-stranded collagen type I peptides related to the collagenase cleavage site

1999

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Synthetic collagen peptides containing larger numbers of Gly-Pro-Hyp repeats are difficult to purify by standard chromatographic procedures. Therefore, efficient strategies are required for the synthesis of higher molecular weight collagen-type peptides. Applying the Fmoc/tBu chemistry, a comparative analysis of the standard stepwise chain elongation procedure on solid support with the procedure based on the use of the synthons Fmoc-Gly-Pro-Hyp(tBu)-OH and Fmoc-Pro-Hyp-Gly-OH was performed. The crude products resulting from the stepwise elongation procedure and from the use of Fmoc-Gly-Pro-Hyp(tBu)-OH clearly revealed large amounts of microheterogeneities that result from incomplete imino acid acylation as well as from diketopiperazine formation with cleavage of Gly-Pro units from the growing peptide chain. Conversely, by the use of the Fmoc-Pro-Hyp-Gly-OH synthon, the quality of the crude products was significantly improved; moreover, protection of the Hyp side chain hydroxyl function is not required using the Fmoc/tBu strategy. With this optimized synthetic procedure, relatively large collagen-type peptides were obtained in satisfactory yields as highly homogeneous compounds.

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Heterotrimeric collagen peptides containing functional epitopes. Synthesis of single-stranded collagen type I peptides related to the collagenase cleavage site

1999

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ChemInform Abstract: DERIVATIVES AND PEPTIDES OF 4‐HYDROXYPROLINE. A COMPENDIUM

Adams¹

1977

Chemischer Informationsdienst

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StereoselectiveO-glycosylation oftrans-4-hydroxy-l-proline derivatives promoted by silver zeolite

Finch

Siriwardena

1989

Glycoconjugate J

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Trans-4-hydroxy-L-proline has been converted to four imino- and carboxyl-blocked derivatives which are suitable for the synthesis of 4-O-glycosyl conjugates. Reaction of these derivatives with 2,3,5-tri-O-benzyl-alpha-L-arabinofuranosyl chloride in the presence of a silver zeolite promoter yielded the blocked beta-furanosyl amino-acid conjugates. Deprotection gave trans-4-(beta-L-arabinofuranosyloxy)-L-proline which was characterised as its crystalline isopropyl ester. 13C-NMR Data are presented for the compounds described.

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Derivatives and Peptides of 4–hydroxyproline: A Compendium

Cited by 4 publications

References 98 publications

Heterotrimeric collagen peptides containing functional epitopes. Synthesis of single-stranded collagen type I peptides related to the collagenase cleavage site

Heterotrimeric collagen peptides containing functional epitopes. Synthesis of single-stranded collagen type I peptides related to the collagenase cleavage site

ChemInform Abstract: DERIVATIVES AND PEPTIDES OF 4‐HYDROXYPROLINE. A COMPENDIUM

StereoselectiveO-glycosylation oftrans-4-hydroxy-l-proline derivatives promoted by silver zeolite

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