2,5-Diiodo-L-histidine hydrochloride
Need Assistance?
  • US & Canada:
    +
  • UK: +

2,5-Diiodo-L-histidine hydrochloride

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category
L-Amino Acids
Catalog number
BAT-006720
CAS number
105158-70-1
Molecular Formula
C6H8ClI2N3O2
Molecular Weight
443.41
2,5-Diiodo-L-histidine hydrochloride
Synonyms
H-2,5-Diiodo-His-OH HCl
Related CAS
6996-16-3 (free base)
Purity
99%
Density
220 °C (dec)
Storage
Store at -20 °C
InChI
InChI=1S/C6H7I2N3O2.ClH/c7-4-3(10-6(8)11-4)1-2(9)5(12)13;/h2H,1,9H2,(H,10,11)(H,12,13);1H/t2-;/m0./s1
InChI Key
VTOVOFBPLIKFQC-DKWTVANSSA-N
Canonical SMILES
C(C1=C(N=C(N1)I)I)C(C(=O)O)N.Cl
1. D-Mannosamine hydrochloride (2-amino-2-deoxy-D-mannose hydrochloride): ionic hydrogen bonding in saccharides involving chloride and aminium ions
Jieye Lin, Allen G Oliver, Anthony S Serianni Acta Crystallogr C Struct Chem. 2022 Apr 1;78(Pt 4):223-230. doi: 10.1107/S2053229622002121. Epub 2022 Mar 5.
D-Mannosamine hydrochloride (2-amino-2-deoxy-D-mannose hydrochloride), C6H14NO5+·Cl-, (I), crystallized from a methanol/ethyl acetate/n-hexane solvent mixture at room temperature in a 4C1 chair conformation that is slightly distorted towards the C3,O5B form. A comparison of the structural parameters of (I) with the corresponding parameters in α-D-glucosamine hydrochloride, (II), and β-D-galactosamine hydrochloride, (III)/(III'), was undertaken to evaluate the effects of ionic hydrogen bonding on structural properties. Three types of ionic hydrogen bonds are present in the crystals of (I)-(III)/(III'), i.e. N+-H...O, N+-H...Cl-, and O-H...Cl-. The exocyclic structural parameters in (I), (II), and (III)/(III') appear to be most influenced by this bonding, especially the exocyclic hydroxy groups, which adopt eclipsed conformations enabled by ionic hydrogen bonding to the chloride anion. Anomeric disorder was observed in crystals of (I), with an α:β ratio of 37:63. However, anomeric configuration appears to exert minimal structural effects; that is, bond lengths, bond angles, and torsion angles are essentially identical in both anomers. The observed disorder at the anomeric C atom of (I) appears to be caused by the presence of the chloride anion and atom O3 or O4 in proximal voids, which provide opportunities for hydrogen bonding to atom O1 in both axial and equatorial orientations.
2. Synthesis of 2-(1,5-diaryl-1,4-pentadien-3-ylidene)-hydrazinecarboximidamide hydrochloride catalyzed by p-dodecylbenzenesulfonic acid in aqueous media under ultrasound irradiation
Ji-Tai Li, Chao Du, Xiao-Ya Xu, Guo-Fen Chen Ultrason Sonochem. 2012 Sep;19(5):1033-8. doi: 10.1016/j.ultsonch.2012.02.009. Epub 2012 Mar 3.
Amidinohydrazone compounds are very important synthetic intermediates and can serve as versatile precursors in synthesis of many natural products and drug molecules. The use of ultrasound, p-dodecylbenzenesulfonic acid (DBSA) and water as solvent improved the synthesis of different 2-(1,5-diaryl-1,4-pentadien-3-ylidene)-hydrazinecarboximidamide hydrochlorides. The best reaction conditions for the condensation of 1,5-diphenyl-1,4-pentadien-3-one with aminoguanidine hydrochloride were as follows: 1,5-diphenyl-1,4-pentadiene-3-one (1, 1 mmol), aminoguanidine hydrochloride (1.1 mmol), DBSA (0.5 mmol), water 10 mL, reaction temperature 25-27°C, irradiation frequency 25 kHz. 2a was achieved in 94% yield within 2h. The other seven amidinohydrazones were obtained in 84-94% yield within 2-3h under the same conditions. Compared to the method involving catalysis by hydrochloric acid in refluxing EtOH, the advantages of present procedure are milder conditions, shorter reaction times, higher yields, and environmental friendly conditions, which make it a useful strategy for the synthesis of analogues.
Online Inquiry
Verification code
Inquiry Basket