N-P-TOSYLGLYCINE Chemical Properties

Melting point:

147-149 °C (lit.)

Boiling point:

430.0±55.0 °C(Predicted)

Density 

1.369±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.41±0.10(Predicted)

color 

White

CAS DataBase Reference

1080-44-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

2935.90.9500

MSDS

• Language:English Provider:SigmaAldrich

N-P-TOSYLGLYCINE Usage And Synthesis

Uses

N-Tosylglycine is a sulfonamide derivative used to synthesize metal complexes which potentially displays antibacterial activity.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

Sodium carbonate (Na2CO3, 1.590 g, 15 mmol) was added to a solution of glycine (12.5 mmol) in water (15 mL) under continuous stirring until completely dissolved. The solution was cooled to -5°C and p-toluenesulfonyl chloride (15 mmol) was added in four batches over 1 hour. The reaction mixture was continued to be stirred at room temperature for about 4 h. The progress of the reaction was monitored using thin layer chromatography (TLC, unfolding agent was MeOH/DCM, 1:9). Upon completion of the reaction, the mixture was acidified with 20% aqueous hydrochloric acid to pH 2. The crystals were collected by diafiltration and washed with pH 2.2 buffer. The pure product 2-(4-methylphenylsulfonamido)acetic acid was dried in a desiccator. The yield was 99.34% (2.8410 g) and the melting point was 88.4-88.6°C. FTIR (KBr, cm-1 ): 3448 (O-H, COOH), 3277 (N-H), 2957 (C-H, aliphatic), 1730 (C=O), 1598, 1440 (C=C), 1354, 1321 (2S=O). 1185 (SO2-NH), 1111, 1094 (C-N, C-O).1H NMR (DMSO-d6) δ: 7.90-7.88 (t, J=6.3 Hz, 1H, NH), 7.65-7.63 (d, J=8.6 Hz, 2H, ArH), 7.34-7.33 (d, J=8.05 Hz, 2H, ArH ), 3.52-3.51 (d, J=5.7 Hz, 2H, CH2), 2.34 (s, 3H, CH3).13C NMR (DMSO-d6) δ: 170.7 (C=O), 143.1, 138.4, 130.0, 127.1 (aryl carbons), 44.3 (CH2), 21.5 (CH3).HRMS-ESI (m/z): 228.0412 ([M-H]-, calculated value: 228.0408).

References

[1] European Journal of Medicinal Chemistry, 2017, vol. 135, p. 349 - 369
[2] PLoS ONE, 2018, vol. 13, # 1,
[3] Journal of the American Chemical Society, 2018, vol. 140, # 17, p. 5834 - 5841
[4] Journal of Molecular Catalysis A: Chemical, 2011, vol. 351, p. 41 - 45
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 31, p. 5618 - 5625

N-P-TOSYLGLYCINE(1080-44-0)Related Product Information

• TOS-PRO-OH
• N-(p-Tolylsulphonyl)-L-glutamic acid
• TOS-LYS(BOC)-OH
• N-(P-TOLUENESULFONYL)-L-PHENYLALANINE
• TOS-ARG-OH
• N-P-TOSYLGLYCINE
• TOS-ARG-OME HCL
• TOS-GLU-OH
• TOS-GLY-OSU
• Tosyl-S-Benzyl-L-cysteine
• TOS-MET-OH
• N-[P-TOLUENESULFONYL]-L-LYSINE METHYL ESTER HYDROCHLORIDE
• 2-([(4-METHYLPHENYL)SULFONYL]AMINO)-2-PHENYLACETIC ACID
• 4-METHYL-2-(TOLUENE-4-SULFONYLAMINO)-PENTANOIC ACID
• NEPSILON-CARBOBENZOXY-NALPHA-TOSYL-L-LYSINE
• 3-METHYL-2-(TOLUENE-4-SULFONYLAMINO)-BUTYRIC ACID
• 3-HYDROXY-2-(TOLUENE-4-SULFONYLAMINO)-PROPIONIC ACID
• 3-AMINO-2-(TOLUENE-4-SULFONYLAMINO)-PROPIONIC ACID