Crystal and molecular structure of L-histidyl-L-serine trihydrate: occurrence of C(alpha)-H...O=C hydrogen bond motif similar to the motif in collagen triple helix and beta-sheets

L-Histidyl-L-serine (HSN) trihydrate, C9H14N4O4-H2O, crystallizes in the orthorhombic space group P2(1)2(1)2(1) with a = 4.865(4), b = 15.604(4), c = 18.918(5) and Z = 4. The crystal structure was solved by direct methods and refined to R1 = 0.070 by a full-matrix least-squares method. The peptide e...

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Bibliographic Details
Published inThe journal of peptide research Vol. 51; no. 4; p. 266
Main Author Padiyar, G S
Format Journal Article
LanguageEnglish
Published Denmark 01.04.1998
Subjects
Animals
Collagen - chemistry
Crystallography, X-Ray
Histidine - chemistry
Humans
Hydrogen
Peptides - chemistry
Protein Folding
Serine - chemistry
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Summary:L-Histidyl-L-serine (HSN) trihydrate, C9H14N4O4-H2O, crystallizes in the orthorhombic space group P2(1)2(1)2(1) with a = 4.865(4), b = 15.604(4), c = 18.918(5) and Z = 4. The crystal structure was solved by direct methods and refined to R1 = 0.070 by a full-matrix least-squares method. The peptide exists in a zwitterionic form, with the N-terminus in a protonated form and the C-terminus in an ionized form. The imidazole ring of histidine in its neutral His(epsilon) tautomeric state has conformational angles chi(1)2 of -53.5(7) degrees and chi(21)1 of -55.4(8) degrees and the serine hydroxyl group has chi(1)2 of 68.2(7) degrees. The conformational angles deviate significantly from those of the dipeptide complexed with glycyl-L-glutamic acid in which the histidine is protonated. A noteworthy feature of the crystal packing is the occurrence of a C(alpha)-H O=C hydrogen bond motif similar to that observed in collagen triple helix and beta-sheets.
ISSN:1397-002X
DOI:10.1111/j.1399-3011.1998.tb00423.x