Fmoc-D-tyrosine

Base Information

• Chemical Name: Fmoc-D-tyrosine
• CAS No.: 112883-29-1
• Molecular Formula: C₂₄H₂₁NO₅
• Molecular Weight: 403.434
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID90426255
• Nikkaji Number: J1.493.030B
• Wikidata: Q72479081
• Mol file: 112883-29-1.mol

Synonyms:FMOC-D-TYR-OH;Fmoc-D-tyrosine;112883-29-1;(((9H-Fluoren-9-yl)methoxy)carbonyl)-D-tyrosine;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxyphenyl)propanoic acid;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoic acid;N-Fmoc-D-Tyr(OH);SCHEMBL1486272;DTXSID90426255;SWZCTMTWRHEBIN-JOCHJYFZSA-N;MFCD00171384;N-(Hydroxymethyl)glycinemonosodiumsalt;AKOS016843663;AM82311;HY-W048703;AS-56486;PD197193;CS-0101017;D86869;EN300-650341;N-(9H-Fluorene-9-ylmethoxycarbonyl)-D-tyrosine;A894516;J-002857;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-hydroxyphenyl)propanoic acid;(r)-2-(((9h-fluoren-9-yl)methoxy)carbonylamino)-3-(4-hydroxyphenyl)propanoic acid

Chemical Property of Fmoc-D-tyrosine

Chemical Property:

• Vapor Pressure: 5.24E-19mmHg at 25°C
• Melting Point: 175-180℃
• Refractive Index: 1.651
• Boiling Point: 672.563 °C at 760 mmHg
• PKA: 2.95±0.10(Predicted)
• Flash Point: 360.553 °C
• PSA: 95.86000
• Density: 1.336 g/cm³
• LogP: 4.31750
• Storage Temp.: Store at RT.
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 403.14197277
• Heavy Atom Count: 30
• Complexity: 580

Purity/Quality:

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

Fmoc-D-Tyr-OH ^*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=CC=C(C=C4)O)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@H](CC4=CC=C(C=C4)O)C(=O)O
• Uses: N-Fmoc-D-tyrosine is an N-Fmoc-protected form of D-Tyrosine (T899970). D-Tyrosine is an unnatural isomer of L-Tyrosine (T899975) that inhibits metabolic activity of Bacillus subtilis. It is known to exhibit antimetabolic effects on rats as well, inhibiting growth and development. D-Tyrosine is also a chiral precursor to biosynthesized inhibitors that have antiinflammatory effects in humans.

Technology Process of Fmoc-D-tyrosine

There total 18 articles about Fmoc-D-tyrosine 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: 100.0%

Fmoc-Tyr(tBu)-OH (71989-38-3,118488-18-9,204384-67-8) → N-Fmoc-Tyr-OH (112883-29-1,92954-90-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.ijpharm.2011.06.007

Reference yield: 89.4%

→ N-Fmoc-Tyr-OH (112883-29-1,92954-90-0)

Guidance literature:

Reference yield: 88.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → N-Fmoc-Tyr-OH (112883-29-1,92954-90-0)

Guidance literature:

With sodium hydrogencarbonate; In acetone; Ambient temperature;

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

L-tyrosine

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(9-fluorenyl)methyl pentafluorophenyl carbonate

Downstream raw materials:

N^α-Fmoc-Tyr-OPfp

Fmoc-Tyr(PO(OMe)2)-OH

(S)-allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-hydroxyphenyl)propanoate

tert-butyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate

Refernces

• 1、 Hendrikse, Simone I. S.,Spaans, Sergio,Meijer,Dankers, Patricia Y. W.. "Supramolecular Platform Stabilizing Growth Factors". . p. 2610 - 2617. Retrieved 2018.
• 2、 Thornton, Kate,Abul-Haija, Yousef M.,Hodson, Nigel,Ulijn, Rein V.. "Mechanistic insights into phosphatase triggered self-assembly including enhancement of biocatalytic conversion rate". . p. 9430 - 9439. Retrieved 2013.
• 3、 Kitagawa,Aida,Fujiwara,Yagami,Futaki,Kogire,Ida,Inoue. "Facile solid-phase synthesis of sulfated tyrosine-containing peptides: Total synthesis of human big gastrin-II and cholecystokinin (CCK)-39". . p. 1 - 10. Retrieved 2001.
• 4、 -. "SUPRAMOLECULAR GEL SUPPORTED ON OPEN-CELL POLYMER FOAM". Page/Page column 16-17; 21. . Retrieved 2021/03/19.
• 5、 Zhu, Lunan,Zhu, Junchen,Sun, Xiaotong,Wu, Yaling,Wang, Huiying,Cheng, Lingping,Shen, Jiawei,Ke, Yanxiong. "Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety". . p. 1080 - 1090. Retrieved 2020/05/25.