(Boc-Cys-OH)

Base Information

• Chemical Name: (Boc-Cys-OH)
• CAS No.: 10389-65-8
• Molecular Formula: C16H28N2O8S2
• Molecular Weight: 440.539
• Hs Code.: 29309090
• NSC Number: 668581,164046
• DSSTox Substance ID: DTXSID80908656
• ChEMBL ID: CHEMBL2001880
• Mol file: 10389-65-8.mol

Synonyms:NSC668581;(Boc-Cys-OH);MFCD00038250;NSC164046;SCHEMBL432222;CHEMBL2001880;DTXSID80908656;AKOS005146494;NSC-164046;NSC-668581;NCI60_023949;SY033223;FT-0653245;N,N'-Bis[tert-butoxy(hydroxy)methylidene]cystine;A800843;L-Cystine,N'-bis[(1,1-dimethylethoxy)carbonyl]-;Cystine, N,N'-bis[(1,1-dimethylethoxy)carbonyl]-;N,N inverted exclamation mark -Bis(Boc)-L-cystine;Cystine,N'-dicarboxy-, N,N'-di-tert-butyl ester, L-;2-(tert-butoxycarbonylamino)-3-[[2-(tert-butoxycarbonylamino)-3-hydroxy-3-oxo-propyl]disulfanyl]propanoic acid;2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxidanyl-3-oxidanylidene-propyl]disulfanyl]propanoic acid;3-[[2-carboxy-2-[[(2-methylpropan-2-yl)oxy-oxomethyl]amino]ethyl]disulfanyl]-2-[[(2-methylpropan-2-yl)oxy-oxomethyl]amino]propanoic acid

Chemical Property of (Boc-Cys-OH)

Chemical Property:

• Melting Point: 140-145 ºC
• Boiling Point: 627.4 °C at 760mmHg
• PKA: 3.17±0.10(Predicted)
• Flash Point: 333.2 °C
• PSA: 201.86000
• Density: 1.313 g/cm³
• LogP: 3.10540
• Storage Temp.: Store at 0-5°C
• Solubility.: Acetic Acid (Sparingly) DMSO (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 13
• Exact Mass: 440.12870820
• Heavy Atom Count: 28
• Complexity: 522

Purity/Quality:

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

N,N''-Di-BOC-L-cystine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CSSCC(C(=O)O)NC(=O)OC(C)(C)C)C(=O)O
• Uses: N,N''-Di-BOC-L-cystine, can be used for the synthesis of Toll-Like Receptor-2 agonists lipopeptides, which are potential vaccine adjuvants.

Technology Process of (Boc-Cys-OH)

There total 25 articles about (Boc-Cys-OH) 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%

L-cystine (56-89-3) + di-tert-butyl dicarbonate (24424-99-5) → di-t-butoxycarbonyl-L-cystine (10389-65-8)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃;

Reference yield: 97.8%

L-Cysteine (52-90-4) + di-tert-butyl dicarbonate (24424-99-5) → di-t-butoxycarbonyl-L-cystine (10389-65-8)

Guidance literature:

With potassium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1016/j.jconrel.2016.05.051

Reference yield: 92.0%

N-(tert-Butyloxycarbonyl)-L-cysteine (20887-95-0) + N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine (76880-29-0) → di-t-butoxycarbonyl-L-cystine (10389-65-8)

Guidance literature:

With phosphate buffer; In acetone; for 2h; 1.) pH= 8, 2.) pH= 3;

DOI:10.1246/cl.1981.737

upstream raw materials:

cysteine disulfide

di-tert-butyl dicarbonate

N-(tert-butyloxycarbonyl) azide

L-cystine

Downstream raw materials:

dicyclohexylamine salt of N-t-butyloxycarbonyl-L-cysteine

C₄₀H₅₄N₄O₁₀S₂

Refernces

• 1、 Salunke, Deepak B.,Connelly, Seth W.,Shukla, Nikunj M.,Hermanson, Alec R.,Fox, Lauren M.,David, Sunil A.. "Design and development of stable, water-soluble, human toll-like receptor 2 specific monoacyl lipopeptides as candidate vaccine adjuvants". . p. 5885 - 5900. Retrieved 2013.
• 2、 Kaneshiro, Todd L.,Ke, Tianyi,Jeong, Eun-Kee,Parker, Dennis L.,Lu, Zheng-Rong. "Gd-DTPA L-cystine bisamide copolymers as novel biodegradable macromolecular contrast agents for MR blood pool imaging". . p. 1285 - 1294. Retrieved 2006.
• 3、 Wang, Feng,Diesendruck, Charles E.. "Effect of disulphide loop length on mechanochemical structural stability of macromolecules". . p. 2143 - 2146. Retrieved 2020.
• 4、 Kaur, Arshpreet,Poonam,Patil, Madhuri T.,Mehta, Surinder K.,Salunke, Deepak B.. "An efficient and scalable synthesis of potent TLR2 agonistic PAM2CSK4". . p. 9587 - 9596. Retrieved 2018.
• 5、 Ma, Xiao-Fei,Sun, Jing,Qiu, Chong,Wu, Yi-Fan,Zheng, Yi,Yu, Min-Zhi,Pei, Xi-Wei,Wei, Lin,Niu, Yu-Jie,Pang, Wen-Hao,Yang, Zhen-Jun,Wang, Jian-Cheng,Zhang, Qiang. "The role of disulfide-bridge on the activities of H-shape gemini-like cationic lipid based siRNA delivery". . p. 99 - 111. Retrieved 2016.
• 6、 Kedika, Bhavani,Patri, Srilakshmi V.. "Synthesis and gene transfer activities of novel serum compatible reducible tocopherol-based cationic lipids". . p. 1146 - 1162. Retrieved 2012.
• 7、 -. "Cystine cholesterol gel factor and preparation method thereof". Paragraph 0040; 0041; 0043. . Retrieved 2021/09/21.
• 8、 Schade, Markus,Merla, Beatrix,Lesch, Bernhard,Wagener, Markus,Timmermanns, Simone,Pletinckx, Katrien,Hertrampf, Torsten. "Highly Selective Sub-Nanomolar Cathepsin S Inhibitors by Merging Fragment Binders with Nitrile Inhibitors". supporting information. p. 11801 - 11808. Retrieved 2020/11/26.