Nalpha-Fmoc-D-histidine

Base Information

• Chemical Name: Nalpha-Fmoc-D-histidine
• CAS No.: 157355-79-8
• Molecular Formula: C21H19 N3 O4
• Molecular Weight: 377.4
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID50427162
• Mol file: 157355-79-8.mol

Synonyms:157355-79-8;FMOC-D-HIS-OH;Nalpha-Fmoc-D-histidine;Fmoc-D-His;FMOC-D-HISTIDINE;(((9H-Fluoren-9-yl)methoxy)carbonyl)-D-histidine;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1H-imidazol-5-yl)propanoic acid;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(1H-imidazol-4-yl)propanoic acid;N-|A-Fmoc-D-histidine;D-Histidine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;SCHEMBL1486208;SCHEMBL20677239;DTXSID50427162;MFCD00237022;AKOS016842939;AM81805;FD21725;HY-W048701;AS-49183;CS-0101015;EN300-81379;Q-101830;Z1227755484;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(1H-imidazol-4-yl)propanoic acid;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(1H-imidazol-4-yl)propanoicacid

Chemical Property of Nalpha-Fmoc-D-histidine

Chemical Property:

• Boiling Point: 706.7±60.0 °C(Predicted)
• PKA: 3.26±0.10(Predicted)
• PSA: 104.31000
• Density: 1.372±0.06 g/cm3(Predicted)
• LogP: 3.33500
• Storage Temp.: 2-8°C
• Solubility.: Acetic Acid (Slightly), Aqueous Base (Slightly), DMSO (Slightly), DMF (Slightly,
• 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:

98.5% ^*data from raw suppliers

N-alpha-Fmoc-D-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-D-histidine is an N-Fmoc-protected form of D-Histidine (H456015). D-Histidine is the unnatural, biologically inactive isomer of L-Histidine (H456010). D-histidine is known to inhibit cell division, and is also used by certain types of bacteria (such as Escherichia coli) as a source of L-Histidine.

Technology Process of Nalpha-Fmoc-D-histidine

There total 1 articles about Nalpha-Fmoc-D-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:

Nα-fmoc-N(im)-trityl-D-histidine → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-histidine (157355-79-8)

Guidance literature:

With trifluoroacetic acid; for 3h;

DOI:10.1016/S0040-4039(00)76938-3

Reference yield:

Fmoc-D-Gln-OH (112898-00-7) + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Trp-OH (35737-15-6) + N-(9-fluorenylmethoxycarbonyl)-D-leucine (35661-60-0,126727-03-5,114360-54-2) + (R)-N-(fluoren-9-ylmethoxycarbonyl)serine (73724-45-5,136083-72-2,116861-26-8) + Fmoc-D-Phe-OH (86123-10-6) + Nα-fluorenyl-9-methoxycarbonyl-D-Met (71989-28-1,144701-23-5,112883-40-6) + Nα-(9H-fluoren-9-ylmethoxycarbonyl)-D-lysine (110990-08-4) + N-Fmoc-D-glutamic acid (104091-09-0) + N-(9-fluorenylmethoxycarbonyl)-D-valine (84624-17-9) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-histidine (157355-79-8) + N-Fmoc-tyrosine + N-9-fluorenylmethoxycarbonyl-D-aspartic acid + Nα-fluoren-9-ylmethoxycarbonyl-L-cysteine (157355-80-1) + Fmoc-D-Asn-OH + Fmoc-D-arginine (130752-32-8) + Fmoc-D-Ile-OH (251316-98-0) → D-(Cys-Leu-Ile-Val-Tyr-Trp-Glu-Met-Glu-Asp-Lys-Asn-Ile-Ile-Gln-Phe-Val-His-Gly-Glu-Glu-Asp-Leu-Lys-Val-Gln-His-Ser-Ser-Tyr-Arg-Gln-Arg)-NHNH2

Guidance literature:

Fmoc-D-arginine; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; at 30 ℃;

With piperidine; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide;

Fmoc-D-Gln-OH; N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Trp-OH; N-(9-fluorenylmethoxycarbonyl)-D-leucine; (R)-N-(fluoren-9-ylmethoxycarbonyl)serine; Fmoc-D-Phe-OH; Nα-fluorenyl-9-methoxycarbonyl-D-Met; N_α-(9H-fluoren-9-ylmethoxycarbonyl)-D-lysine; N-Fmoc-D-glutamic acid; N-(9-fluorenylmethoxycarbonyl)-D-valine; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-histidine; N-Fmoc-tyrosine; N-9-fluorenylmethoxycarbonyl-D-aspartic acid; Nα-fluoren-9-ylmethoxycarbonyl-L-cysteine; Fmoc-D-Asn-OH; Fmoc-D-Ile-OH; Further stages;

DOI:10.1002/anie.201506225

Reference yield:

Fmoc-D-Gln-OH (112898-00-7) + (R)-N-(fluoren-9-ylmethoxycarbonyl)serine (73724-45-5,136083-72-2,116861-26-8) + Fmoc-D-Phe-OH (86123-10-6) + Nα-(9H-fluoren-9-ylmethoxycarbonyl)-D-lysine (110990-08-4) + (R)-Pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (71989-31-6,109425-54-9,144829-96-9,101555-62-8) + (((9H-fluoren-9-yl)methoxy)carbonyl)-D-threonine (157355-81-2) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-histidine (157355-79-8) + N-Fmoc-tyrosine + N-9-fluorenylmethoxycarbonyl-D-aspartic acid + Fmoc-D-Asn-OH + Fmoc-D-arginine (130752-32-8) → D-(Asn-Tyr-Ser-Lys-Pro-Thr-Asp-Arg-Gln-Tyr-His-Phe)-NH2

Guidance literature:

Fmoc-D-Phe-OH; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; at 30 ℃;

With piperidine; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide;

Fmoc-D-Gln-OH; (R)-N-(fluoren-9-ylmethoxycarbonyl)serine; N_α-(9H-fluoren-9-ylmethoxycarbonyl)-D-lysine; (R)-Pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester; (((9H-fluoren-9-yl)methoxy)carbonyl)-D-threonine; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-histidine; N-Fmoc-tyrosine; N-9-fluorenylmethoxycarbonyl-D-aspartic acid; Fmoc-D-Asn-OH; Fmoc-D-arginine; Further stages;

DOI:10.1002/anie.201506225

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