Compound monograph
Desmopressin
Desmopressin is a synthetic cyclic peptide construction containing eight amino-acid units and an N-terminal 3-mercaptopropanoyl unit. Its conventional numbering spans nine positions. This record describes the anhydrous parent without acetate or water of crystallization.
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Identity & nomenclature
Desmopressin is a synthetic cyclic peptide construction containing eight amino-acid units and an N-terminal 3-mercaptopropanoyl unit. Its conventional numbering spans nine positions. This record describes the anhydrous parent without acetate or water of crystallization.
The abbreviation dDAVP identifies the D-Arg8 compound in the structural literature. The abbreviation dAVP is also used for its L-Arg8 counterpart and is not retained as an alias. The position-1 unit is 3-mercaptopropanoyl, rather than cysteine.
Declared aliases and development codes: dDAVP, 1-deamino-8-D-arginine vasopressin, 1-desamino-8-D-arginine vasopressin.
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Molecular properties
| Three-letter sequence | Mpa–L-Tyr–L-Phe–L-Gln–L-Asn–L-Cys–L-Pro–D-Arg–Gly–NH2 |
|---|
Mpa denotes 3-mercaptopropanoyl, an achiral acyl unit at conventional position 1; Tyr is position 2. The NH2 token denotes the terminal amide and is not another residue. Standard one-letter notation cannot specify Mpa1 and D-Arg8 faithfully. The N-terminal acyl chemistry and Mpa1-Cys6 disulfide are outside the automated sequence-formula model.
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Structural characteristics
Position 1 and glycine at position 9 are achiral. The specified amino-acid stereocentres include D-Arg at position 8. Average molecular mass remains unestablished under the dossier evidence requirements; the molecular formula and mass fields are both withheld.
- Intramolecular disulfide between Mpa1 and L-Cys6
- D-Arg at position 8
Terminal features: N-terminal 3-mercaptopropanoyl acyl unit; no free N-terminal alpha-amino group, C-terminal amidation at Gly9.
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Molecular targets & mechanisms
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Analytical considerations
Elemental composition and mass alone cannot distinguish this molecule from its L-Arg8 counterpart. The cited NMR characterization does not certify the identity or stereochemical purity of an untested sample.
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Verified bibliography
- Conformation of desmopressin, an analogue of the peptide hormone vasopressin, in aqueous solution as determined by NMR spectroscopy.
Walse B, Kihlberg J, Drakenberg T
European journal of biochemistry · 1998-03-15 · Journal Article
current
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Methodology & citation verification
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