BOC-CYS-OH Chemical Properties

Melting point:

67-70°C

Boiling point:

361.4±37.0 °C(Predicted)

Density 

1?+-.0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol

form 

Solid

pka

3.57±0.10(Predicted)

color 

White to Off-White

optical activity

[α]20/D +8.0±1.5°, c = 1% in ethanol

BRN 

2450705

InChI

InChI=1S/C8H15NO4S/c1-8(2,3)13-7(12)9-5(4-14)6(10)11/h5,14H,4H2,1-3H3,(H,9,12)(H,10,11)/t5-/m0/s1

InChIKey

ATVFTGTXIUDKIZ-YFKPBYRVSA-N

SMILES

C(O)(=O)[C@H](CS)NC(OC(C)(C)C)=O

CAS DataBase Reference

20887-95-0(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich

BOC-CYS-OH Usage And Synthesis

Chemical Properties

light yellowliquid

Uses

Boc-L-cysteine is the protected form of L-Cysteine (C995000), a non-essential α-amino acid that is biosynthesized in humans. L-Cysteine is also a bicarbonate-sensitive endogenous excitotoxin in rats and possibly humans.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of (R)-2-((tert-butoxycarbonyl)amino)-3-mercaptopropionic acid from N,N'-bis(Boc)-L-cystine: N,N'-bis(Boc)-L-cystine (2.51 mmol) was dissolved in a solvent mixture of tetrahydrofuran (29.2 mL) and water (0.8 mL). Tributylphosphine (2.76 mmol) was added to the solution under ice bath cooling conditions. The reaction mixture was gradually warmed up to room temperature and stirred continuously at this temperature for 1 hour. Upon completion of the reaction, ethyl acetate (20 mL) and 10% aqueous citric acid (10 mL) were added to the reaction mixture for extraction and separation. The organic phase was collected and washed with saturated aqueous saline solution (20 mL). Subsequently, the organic phase was concentrated and the resulting residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate mixed solvent) to afford the target compound 22 as an oily product. Yield: 99%. ESI MS m/z 220.1 [M-H]-; 1H NMR (400 MHz, CDCl3) δ: 5.47 (1H, brs), 4.65 (1H, brs), 3.09-2.97 (2H, m), 1.48 (9H, s).

References

[1] Patent: US2012/282386, 2012, A1. Location in patent: Page/Page column 15
[2] Journal of Nanoparticle Research, 2017, vol. 19, # 6,
[3] Angewandte Chemie, 1993, vol. 105, # 2, p. 311 - 313
[4] Chemische Berichte, 1969, vol. 102, p. 1048 - 1052
[5] Protein and Peptide Letters, 2014, vol. 21, # 12, p. 1257 - 1264

BOC-CYS-OH(20887-95-0)Related Product Information

• BOC-CYS(ET)-OH
• BOC-CYS-OH
• BOC-CYS(4-MEOBZL)-OH
• BOC-S-TERT-BUTYLMERCAPTO-L-CYSTEINE
• BOC-CYS(ME)-OH
• BOC-L-THIAZOLIDINE-4-CARBOXYLIC ACID
• BOC-CYS(ACM)-OH
• BOC-PEN(MOB)-OH
• Boc-S-Benzyl-L-cysteine
• Boc-S-(4-methylbenzyl)-L-cysteine
• (Boc-Cys-OH)2 (Disulfide bond),(BOC-CYS-OH)2
• N-Boc-S-Trityl-L-cysteine
• BOC-CYS(DPM)-OH
• BOC-CYS(TBU)-OH
• BOC-CYS(FM)-OH
• BOC-S-(4-METHOXYBENZYL)-L-CYSTEINE DICYCLOHEXYLAMINE SALT
• BOC-CYS(BZL)-ONP
• BOC-CYS(3,4-DIMETHYLBENZYL)-OH