56586-95-9

Basic information

• Product Name: CYCLO(-HIS-PHE)
• Synonyms: CYCLO(-HIS-PHE);cyclo(histidine-phenylalanine)
• CAS NO: 56586-95-9
• Molecular Formula: C₁₅H₁₆N₄O₂
• Molecular Weight: 284.31
• Product Categories: Dipeptides;Dipeptides and Tripeptides;Peptides
• Mol File: 56586-95-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 259-263 °C (decomp)
• Boiling Point: 722.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.294±0.06 g/cm3(Predicted)
• Storage Temp.: −20°C
• PKA: 12.71±0.60(Predicted)
• CAS DataBase Reference: CYCLO(-HIS-PHE)(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLO(-HIS-PHE)(56586-95-9)
• EPA Substance Registry System: CYCLO(-HIS-PHE)(56586-95-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 56586-95-9(Hazardous Substances Data)

Usage

General Description

CYCLO(-HIS-PHE) is a cyclic dipeptide composed of the amino acid histidine and phenylalanine, linked together by a peptide bond to form a ring structure. This cyclic dipeptide has been found to possess various biological activities, including antimicrobial, antitumor, and antioxidant properties. It has also been shown to have potential therapeutic applications in the treatment of cancer and neurodegenerative diseases. Additionally, CYCLO(-HIS-PHE) has been studied for its ability to modulate the immune response and inflammation, making it a promising candidate for the development of novel drugs and pharmaceuticals.

Upstream product

• 17791-52-5 N-(tert-butoxycarbonyl)-L-histidine 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 1161-13-3 N-Cbz-L-Phe 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 20866-46-0 N,1'-bis[(1,1-dimethylethoxy)carbonyl]-L-histidine 
• 2578-84-9 N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester 
• 76524-86-2 L-Phe-L-His-OMe 
• 16689-13-7 N-(Benzyloxycarbonyl)-(S)-phenylalanyl-(S)-histidine Methyl Ester 
• 16689-13-7 benzyloxycarbonyl-(S)-phenylalanyl-(S)-histidine methyl ester 
• 7389-87-9 (S)-histidine methyl ester dihydrochloride 
• 1499-46-3 L-Histidine methyl ester 

Relevant articles and documents

Five- and six-membered nitrogen-containing compounds as selective carbonic anhydrase activators

It has been proven that specific isoforms of human carbonic anhydrase (hCA) are able to fine-tune physiological pathways connected to signal processing, and that decreased CAs expression negatively influences cognition, leading to mental retardation, Alzheimer’s disease, and aging-related cognitive dysfunctions. For this reason, a small library of natural and synthetic nitrogen containing cyclic derivatives was assayed as activators of four human isoforms of carbonic anhydrase (hCA I, II, IV and VII). Most of the compounds activated hCA I, IV and VII in the micromolar range, with KAs ranging between 3.46 and 80.5 μM, whereas they were not active towards hCA II (KAs > 100 μM). Two natural compounds, namely L-(+)-ergothioneine (1) and melatonin (2), displayed KAs towards hCA VII in the nanomolar range after evaluation by a CO2 hydration method in vitro, showing a rather efficient and selective activation profile with respect to histamine, used as a reference compound. Corroborated with the above in vitro findings, a molecular modelling in silico approach has been performed to correlate these biological data, and to elucidate the binding interaction of these activators within the enzyme active site.

Biomimetic catalysis of diketopiperazine and dipeptide syntheses

Modular supramolecular catalysts with a coiled-coil peptide scaffold, designed to mimic nonribosomal peptide synthetases, catalyze the formation of diketopiperazines and linear dipeptides for several aminoacyl substrates (see scheme). The nature of the ac

The Cyclic Dipeptide cyclo as a Catalyst for Asymmetric Addition of Hydrogen Cyanide to Aldehydes

cyclo (cyclo, 1) catalyzes the addition of hydrogen cyanide to benzaldehyde in toluene at -20 deg C to afford (R)-mandelonitrile with enantiomeric excess of 97 percent in high yield. cyclo gives (S)-mandelonitrile. cyclo (1) exhibits a broad substrate specificity, and a variety of aldehydes (3a-r) such as m-methoxybenzaldehyde (3c), 6-methoxy-2-naphthaldehyde (3k), and isobutyraldehyde (3o) similarly afforded the corresponding cyanohydrins with high enantiopurities (97 percent ee for 3c, 93 percent ee for 3k, 71 percent ee for 3o). (R)-Mandelonitrile thus obtained was successfully converted to various chiral synthons such as mandelic acid (7), methyl mandelate (8), and 2-amino-1-phenylethanol (9) without any racemization.