FMOC-L-Histidine

Base Information

• Chemical Name: FMOC-L-Histidine
• CAS No.: 116611-64-4
• Molecular Formula: C21H19N3O4
• Molecular Weight: 377.4
• Hs Code.: 29332900
• European Community (EC) Number: 824-663-8
• DSSTox Substance ID: DTXSID40427070
• Nikkaji Number: J263.945I
• Wikidata: Q72478447
• Mol file: 116611-64-4.mol

Synonyms:116611-64-4;Fmoc-His-OH;FMOC-L-Histidine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(1H-imidazol-4-yl)propanoic acid;FMOC-HIS;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1H-imidazol-5-yl)propanoic acid;(((9H-Fluoren-9-yl)methoxy)carbonyl)-L-histidine;L-Histidine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;N-|A-Fmoc -L-histidine;MFCD00190885;N-|A-Fmoc-L-histidine;Fmoc-His-OH, AldrichCPR;N alpha -Fmoc-L-histidine;SCHEMBL1405811;DTXSID40427070;SIRPVCUJLVXZPW-IBGZPJMESA-N;AKOS012614848;AKOS015837335;AKOS037643742;AM81806;HY-W048911;AS-35004;PD197205;CS-0101093;EN300-81310;A893554;Q-101829;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(1H-imidazol-4-yl)propanoic acid;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(1H-imidazol-4-yl)propanoicacid;(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-(1H-IMIDAZOL-4-YL)PROPANOIC ACID

Chemical Property of FMOC-L-Histidine

Chemical Property:

• Melting Point: 171-174 °C(Solv: methanol (67-56-1); water (7732-18-5))
• Boiling Point: 706.688 °C at 760 mmHg
• PKA: 3.26±0.10(Predicted)
• Flash Point: 381.191 °C
• PSA: 104.31000
• Density: 1.372 g/cm³
• LogP: 3.33500
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), DMF (Slightly, Sonicated), Methanol (Very Slightly, Heated)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 377.13755610
• Heavy Atom Count: 28
• Complexity: 550

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-alpha-Fmoc-L-histidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CN=CN4)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CN=CN4)C(=O)O
• Uses: Nα-Fmoc-L-histidine is an N-Fmoc-protected form of L-Histidine (H456010). L-Histidine is an essential amino acid that plays an important role in mitochondrial glutamine transport and has potential of abolishing oxidative stress caused by brain edema.L-Histidine promotes zinc uptake in human erythrocyes and also has potential as an antioxidant therapy for acute mammary inflammation in cattle.

Technology Process of FMOC-L-Histidine

There total 5 articles about FMOC-L-Histidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

Nα-(Fluoren-9-ylmethoxycarbonyl)-N(im)-(tert-butyloxycarbonyl)-L-histidine (159631-28-4,81379-52-4) → (9-fluorenylmethoxycarbonyl)-L-histidine (116611-64-4)

Guidance literature:

With tin(IV) chloride; In ethyl acetate; for 0.416667h; Ambient temperature;

DOI:10.1039/cc9960002509

Reference yield: 93.0%

Fmoc-His(Trt)-OH (109425-51-6) → (9-fluorenylmethoxycarbonyl)-L-histidine (116611-64-4)

Guidance literature:

With sodium thiosulfate; magnesium iodide; In 2-methyltetrahydrofuran; at 120 ℃; for 2.5h; chemoselective reaction; Microwave irradiation; Inert atmosphere;

DOI:10.1002/bip.22908

Reference yield:

C24H22N3O6PS → (9-fluorenylmethoxycarbonyl)-L-histidine (116611-64-4)

Guidance literature:

With water; In aq. phosphate buffer; at 80 ℃; for 14h; Solvent; Reagent/catalyst; Temperature;

DOI:10.1021/jacs.8b11912

upstream raw materials:

N_α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(tert-butyloxycarbonyl)-L-histidine

(fluorenylmethoxy)carbonyl chloride

L-histidine

Fmoc-His(Trt)-OH

Downstream raw materials:

H-His-Trp-Gly-Phe-OH

H-Phe-Gly-Trp-His-OH

C₄₅H₆₄N₄O₉Si₂

Refernces

• 1、 Frank, Robert,Schutkowski, Mike. "Extremely mild reagent for Boc deprotection applicable to the synthesis of peptides with thioamide linkages". . p. 2509 - 2510. Retrieved 1996.
• 2、 Monty, Olivier B. C.,Simmons, Nicholas,Chamakuri, Srinivas,Matzuk, Martin M.,Young, Damian W.. "Solution-Phase Fmoc-Based Peptide Synthesis for DNA-Encoded Chemical Libraries: Reaction Conditions, Protecting Group Strategies, and Pitfalls". . p. 833 - 843. Retrieved 2020.
• 3、 -. "THIOPHOSPHORODICHLORIDATE REAGENTS FOR CHEMOSELECTIVE HISTIDINE BIOCONJUGATION". Paragraph 0109. . Retrieved 2020/06/10.