3253-17-6

Basic information

• Product Name: H-ALA-HIS-OH
• Synonyms: H-ALA-HIS-OH;ALA-HIS;N-L-alanyl-L-histidine;alanylhistidine;L-alanyl-histidine;2-(2-aminopropanoylamino)-3-(1H-imidazol-5-yl)propanoic acid;2-(2-azanylpropanoylamino)-3-(1H-imidazol-5-yl)propanoic acid;2-(alanylamino)-3-(1H-imidazol-5-yl)propionic acid
• CAS NO: 3253-17-6
• Molecular Formula: C₉H₁₄N₄O₃
• Molecular Weight: 226.23
• EINECS: 221-845-3
• Product Categories: Dipeptides;Dipeptides and Tripeptides;Peptides
• Mol File: 3253-17-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 629.5 °C at 760mmHg
• Flash Point: 334.5 °C
• Appearance: /
• Density: 1.372 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: −20°C
• PKA: 2.87±0.10(Predicted)
• CAS DataBase Reference: H-ALA-HIS-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-ALA-HIS-OH(3253-17-6)
• EPA Substance Registry System: H-ALA-HIS-OH(3253-17-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 16-26-36
• WGK Germany: 3
• Hazardous Substances Data: 3253-17-6(Hazardous Substances Data)

Usage

Uses

L-Alanyl-L-histidine is a peptide food compound used for suppressing hepatic lipogenesis.

Definition

ChEBI: A dipeptide formed from L-alanyl and L-histidine residues.

InChI:InChI=1/C9H14N4O3/c1-5(10)8(14)13-7(9(15)16)2-6-3-11-4-12-6/h3-5,7H,2,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)/t5-,7-/m0/s1

Upstream product

• 79458-92-7 N^α-(N-benzyloxycarbonyl-alanyl)-histidine 
• 17350-66-2 N-benzyloxycarbonylalaninehydrazid 
• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 

Downstream Products

• 56-41-7 L-alanin 
• 71-00-1 L-histidine 

Relevant articles and documents

Cu(II) Binding to the Peptide Ala-His-His, a Chimera of the Canonical Cu(II)-Binding Motifs Xxx-His and Xxx-Zzz-His

Peptides and proteins with the N-terminal motifs NH2-Xxx-His and NH2-Xxx-Zzz-His form well-established Cu(II) complexes. The canonical peptides are Gly-His-Lys and Asp-Ala-His-Lys (from the wound healing factor and human serum albumin, respectively). Cu(II) is bound to NH2-Xxx-His via three nitrogens from the peptide and an external ligand in the equatorial plane (called 3N form here). In contrast, Cu(II) is bound to NH2-Xxx-Zzz-His via four nitrogens from the peptide in the equatorial plane (called 4N form here). These two motifs are not mutually exclusive, as the peptides with the sequence NH2-Xxx-His-His contain both of them. However, this chimera has never been fully explored. In this work, we use a multispectroscopic approach to analyze the Cu(II) binding to the chimeric peptide Ala-His-His (AHH). AHH is capable of forming the 3N- and 4N-type complexes in a pH dependent manner. The 3N form predominates at pH ～ 4-6.5 and the 4N form at ～ pH 6.5-10. NMR experiments showed that at pH 8.5, where Cu(II) is almost exclusively bound in the 4N form, the Cu(II)-exchange between AHH or the amidated AHH-NH2 is fast, in comparison to the nonchimeric 4N form (AAH). Together, the results show that the chimeric AHH can access both Cu(II) coordination types, that minor changes in the second (or further) coordination sphere can impact considerably the equilibrium between the forms, and that Cu kinetic exchange is fast even when Cu-AHH is mainly in the 4N form.

Amino Acids and Peptides. III. Synthesis of Model Peptides Related to Cytochrome P-450

Various tetra- and pentapeptides with Cys and Ser (Thr, Tyr, His) at the N- and C-terminals, respectively, were synthetized as model peptides of the apoprotein of cytochrome P-450.The optical spectra of synthetic peptide-hemin complexes were measured and the results are discussed.Keywords - cytochrome P-450; synthetic Cys-containing peptide; peptide-hemin complex; optical spectrum of peptide-hemin complex