(S)-N-Fmoc-Allylglycine Chemical Properties

Melting point:

137.1 °C

Boiling point:

473.68°C (rough estimate)

Density 

1.2486 (rough estimate)

refractive index 

1.5800 (estimate)

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.72±0.10(Predicted)

color 

White to Off-White

optical activity

-8.633° (C=0.01 g/ml, DMF)

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C20H19NO4/c1-2-7-18(19(22)23)21-20(24)25-12-17-15-10-5-3-8-13(15)14-9-4-6-11-16(14)17/h2-6,8-11,17-18H,1,7,12H2,(H,21,24)(H,22,23)/t18-/m0/s1

InChIKey

YVBLQCANYSFEBN-SFHVURJKSA-N

SMILES

C(O)(=O)[C@@H](NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O)CC=C

CAS DataBase Reference

146549-21-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

(S)-N-Fmoc-Allylglycine Usage And Synthesis

Chemical Properties

white to almost white powder

Uses

2-Allyl-N-Fmoc-L-glycine is potentially useful for solid phase peptide synthesis techniques. 2-Allyl-N-Fmoc-L-glycine compound could be useful as an unusual amino acid analog to aid in the deconvolution of protein structure and function. Reagent in the synthesis of a Dicarba-Analog of Octreotide.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of Fmoc-L-allylglycine from (S)-(-)-2-amino-4-pentenoic acid and 9-fluorenylmethyl-N-succinimidyl carbonate is as follows: 7.14.1 Preparation of 2-N-fluorenylmethoxycarbonylaminopent-4-enoic acid (Fmoc-Hag-OH) Allylglycine derivatives were prepared according to Paquet's method. Fmoc-OSu (14.60 g, 43.3 mmol) was added to a solution of L-allylglycine (5.00 g, 43.5 mmol) and NaHCO3 (18.20 g, 0.22 mol) in acetone:water (200 mL) mixture under stirring conditions. The resulting white suspension was stirred at room temperature for 20 h. Complete consumption of the raw material was confirmed by thin layer chromatography (TLC, silica gel plate, light petroleum ether:ethyl acetate = 1:1) analysis. The reaction mixture was acidified to pH 2 with concentrated hydrochloric acid and acetone was removed under reduced pressure. The resulting suspension was extracted with dichloromethane (DCM, 3×75 mL), and the organic phases were combined, washed sequentially with dilute hydrochloric acid (1M, 2×50 mL), water (2×50 mL), dried (MgSO4), and concentrated under reduced pressure to afford the target product Fmoc-amino acid 96 as a colorless solid (14.01 g, 96% yield) with a melting point of 137-138 °C (literature value (134-136°C). IR spectrum (KBr, cm-1): 3484 (s), 3198 (bs), 3085 (m), 2967 (m), 2923 (m), 1723 (s), 1644 (m), 1525 (s), 1478 (w), 1449 (s), 1396 (m), 1340 (m), 1233 (s), 1189 (s). 1099(m), 1048(s), 998(w), 966(w), 943(m), 924(w), 850(m), 781(m), 761(s), 740(m), 648(w), 623(m), 582(m), 560(w), 540(m), 424(w). 1H NMR (400MHz, CDCl3): δ 2.52-2.70 (m, 2H, H3), 4.23 (t, J=6.9Hz, 1H, H9'), 4.42 (d, J=6.9Hz, 2H, CH2O), 4.52 (m, 1H, H2), 5.13-5.23 (m, 2H, H5), 5.31 (bd, J= 7.8 Hz, 1H, NH), 5.75 (m, 1H, H4), 6.63 (bs, 1H, OH), 7.31 (td, J=7.4,0.8 Hz, 2H, H2',7'), 7.38 (t, J=7.4 Hz, 2H, H3',6'), 7.52-7.63 (m, 2H, H1',8'), 7.76 (d, J = 7.5 Hz, 2H, H4',5'), no exchangeable protons (OH) were observed. 13C NMR (100 MHz, CDCl3): δ 36.7 (C3), 47.5 (C9'), 53.4 (C2), 68.1 (CH2O), 122.0 (C5), 120.1 (C2',7'), 125.4 (C3',6'), 127.9 (C1',8'), 128.0 (C4',5') 131.1 (C4), 141.7 (C8'a,9'a), 144.0 (C4'a,4'b), 156.3 (OCONH), 176.4 (C1). Mass spectrum (ESI+, MeOH): m/z 338.4 ([M+H]+, calculated value 338.1, C20H20NO4), 360.3 ([M+Na]+, calculated value 360.1, C20H19NNaO4). The spectral data are in agreement with those reported in the literature.

References

[1] Patent: US9102708, 2015, B2. Location in patent: Page/Page column 151
[2] Organic Letters, 2004, vol. 6, # 19, p. 3285 - 3288
[3] Tetrahedron, 2014, vol. 70, # 42, p. 7621 - 7626

(S)-N-Fmoc-Allylglycine(146549-21-5)Related Product Information

• Allyl hexanoate
• 4-Aminophenylacetic acid
• Allyl chloride
• Allyl bromide
• Allyl glycidyl ether
• Fmoc-Lys(Boc)-OH
• 4-Hydroxy-D-(-)-2-phenylglycine
• 6-Aminocaproic acid
• Glycine
• METHOXYCARBONYLSULFENYL CHLORIDE
• Sodium allylsulfonate
• L-Fmoc-Aspartic acid alpha-tert-butyl ester
• Sodium glycinate
• 9-Fluorenylmethyl chloroformate
• 2-Aminophenol
• Tris(hydroxymethyl)aminomethane
• Fmoc-OSu
• Fmoc-Asp(OtBu)-OH