6533b7cffe1ef96bd1258444

RESEARCH PRODUCT

Two phosphonodehydrotripeptides: Boc0–Gly1–Δ(Z)Phe2–α‐Abu3PO3Me2 and Boc0–Gly1–Δ(Z)Phe2–α‐Nva3PO3Et2

Elżbieta LisMarta OtrębaTadeusz LisMarek LisowskiMaciej MakowskiAnna Brzuszkiewicz

subject

chemistry.chemical_classificationEthanolHydrogen bondStereochemistryHydrogen moleculeGeneral MedicineCrystal structureGeneral Biochemistry Genetics and Molecular BiologyAmino acidCrystalSolventchemistry.chemical_compoundResidue (chemistry)chemistry

description

The present paper reports the crystal structures of two short phosphonotripeptides (one in two crystal forms) containing one ΔPhe (dehydrophenylalanine) residue, namely dimethyl (3-{[tert-butoxycarbonylglycyl-α,β-(Z)-dehydrophenylalanyl]amino}propyl)phosphonate, Boc0–Gly1–Δ(Z)Phe2–α-Abu3PO3Me2, C21H32N3O7P, (I), and diethyl (4-{[tert-butoxycarbonylglycyl-α,β-(Z)-dehydrophenylalanyl]amino}butyl)phosphonate, Boc0–Gly1–Δ(Z)Phe2–α-Nva3PO3Et2, as the propan-2-ol monosolvate 0.122-hydrate, C24H38N3O7P·C3H8O·0.122H2O, (II), and the ethanol monosolvate 0.076-hydrate, C24H38N3O7P·C2H6O·0.076H2O, (III). The crystals of (II) and (III) are isomorphous but differ in the type of solvent. The phosphono group is linked directly to the last Cαatom in the main chain for all three peptides. All the amino acids aretranslinked in the main chains. The crystal structures exhibit no intramolecular hydrogen bonds and are stabilized by intermolecular hydrogen bonds only.

10.1107/s0108270113002539https://doi.org/10.1107/S0108270113002539