Glycine: The Smallest Anti-Inflammatory Micronutrient

Abstract

Glycine is a non-essential amino acid with many functions and effects. Glycine can bind to specific receptors and transporters that are expressed in many types of cells throughout an organism to exert its effects. There have been many studies focused on the anti-inflammatory effects of glycine, including its abilities to decrease pro-inflammatory cytokines and the concentration of free fatty acids, to improve the insulin response, and to mediate other changes. However, the mechanism through which glycine acts is not clear. In this review, we emphasize that glycine exerts its anti-inflammatory effects throughout the modulation of the expression of nuclear factor kappa B (NF-κB) in many cells. Although glycine is a non-essential amino acid, we highlight how dietary glycine supplementation is important in avoiding the development of chronic inflammation.

Organo-Photoredox Catalyzed gem-Difluoroallylation of Glycine and Glycine Residue in Peptides

“…55.7 mg, 66% yield, R f = 0.6, PE/EtOAc = 25:1, yellow oil; 1 H NMR (400 MHz, CDCl 3 ) δ 7.61 (d, J = 7.5 Hz, 4H), 7.46 (t, J = 7.1 Hz, 2H), 7.39 (d, J = 7.3 Hz, 3H), 7.01 (t, J = 7.3 Hz, 1H), 6.54 (d, J = 7.5 Hz, 1H), 6.30 (d, J = 7.6 Hz, 2H), 4.13−4.01 (m, 3H), 2.92 (s, 2H), 2.21 (s, 3H), 1.22 (t, J = 7.1 Hz, 3H); 19 F NMR (377 MHz, CDCl 3 ) δ −89.00 (d, J = 37.8 Hz), −89.34 (d, J = 37.9 Hz); 13 C { 1 H} NMR (100 MHz, CDCl 3 ) δ 173. 2,154.7 (dd,J = 289.7,287.0 Hz),146.4,140.7,140.6,139.2,131.7 (t,J = 3.5 Hz),129.3,129.0,127.7,127.4,127.2,119.6,114.5,110.9,88.9 Ethyl 4-( [1,-4-yl)-5,5-difluoro-2-(mesitylamino)pent-4-enoate (3e). 34.9 mg, 39% yield, R f = 0.6, PE/EtOAc = 25:1, colorless oil; 1 H NMR (400 MHz, CDCl 3 ) δ 7.63 (t, J = 5.8 Hz, 4H), 7.48 (t, J = 7.2 Hz, 2H), 7.42−7.37 (m, 3H), 6.81−6.77 (m, 2H), 4.04−3.99 (m, 2H), 3.87 (t, J = 7.0 Hz, 1H), 2.92 (d, J = 6.4 Hz, 2H), 2.23−2.16 (m, 9H), 1.18 (t, J = 7.1 Hz, 3H); 19 F NMR (377 MHz, CDCl 3 ) δ −88.98 (d, J = 37.9 Hz), −89.28 (d, J = 37.8 Hz); 13 C { 1 H} NMR (100 MHz, CDCl 3 ) δ 174.3, 154.5 (dd, J = 290.2, 287.0 Hz), 141.0, 140.6 (d, J = 4.6 Hz), 131.8 (t, J = 3.6 Hz), 131.4,129.8,129.6,129.0 (d,J = 5.3 Hz), 128.9 (t, J = 2.9 Hz), 127.8,127.4,127.3,127.2,89.0 (dd,J = 20.9,15.4 Hz),61.2,58.5,32.5,20.7,18.7,14.2 Ethyl 4-( [1,-4-yl)-2-((4-chlorophenyl)amino)-5,5-difluoropent-4-enoate (3f).…”

“…41.6 mg, 43% yield, R f = 0.5, PE/EtOAc = 25:1, yellow oil; 1 H NMR (400 MHz, CDCl 3 ) δ 7.85 (d, J = 7.7 Hz, 2H), 7.66−7.58 (m, 4H), 7.48 (t, J = 7.1 Hz, 2H), 7.40− 7.36 (m, 3H), 6.45 (d, J = 7.9 Hz, 2H), 4.62 (d, J = 8.5 Hz, 1H), 4.35−4.30 (m, 2H), 4.24−4.00 (m, 3H), 3.09−2.89 (m, 2H), 1.37 (t, J = 6.7 Hz, 3H), 1.24 (t, J = 7.0 Hz, 3H); 19 F NMR (377 MHz, CDCl 3 ) δ −88.64 (d, J = 37.2 Hz), −89.15 (d, J = 37.2 Hz); 13 C { 1 H} NMR (100 MHz, CDCl 3 ) δ 172. 2,166.8,154.7 (dd,J = 290.3,287.5 Hz),149.9,140.8,140.4,131.6,131.4 (t, J = 3.4 Hz), 129.0 (t, J = 2.7 Hz), 127.7,127.4,127.2,120.0,112.2,88.5 (dd,J = 21.1,16.2 Hz),61.8,60.5,54.5,53.6,31.2,14.6,14.2; HRMS (ESI-TOF) m/z: [M + H] + Calcd for C 28 H 28 F 2 NO 4 480.1981;Found 480.1976. Ethyl 4-([1,1′-Biphenyl]-4-yl)-5,5-difluoro-2-((4-(trifluoromethyl)phenyl)amino)pent-4-enoate (3j).…”

“…= 1:1, R f = 0.6, PE/EtOAc = 10:1, white solid; mp 178−180 °C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.59−7.53 (m, 3H), 7.45 (t, J = 7. 1 Hz,2H),1H),7.30 (d,J = 7.6 Hz,2H),7.23 (d,J = 8.7 Hz,2H),3H) 2,171.8,154.7 (dd,J = 290.5,286.7 Hz),146.3,140.8,140.5,135.5,131.1 (t,J = 3.6 Hz),129.5,129.3,129.0,128.7,127.7,127.6,127.2,119.6,113.8,89.2 (dd,J = 20.9,15.8 Hz),58.1,52.6,52.5,38.1,31.9,29.9 3,172.1,154.8 (dd,J = 290.5,286.7 Hz),146.6,140.9,140.5,131.1 (t,J = 3.6 Hz),129.5,129.0,127.7,127.6,127.2,119.6,114.0,89.3 (dd,J = 20.6,…”

“…Peptides belong to an important class of biomolecules with crucial roles in diverse living processes, such as immune defense and cell proliferation and differentiation . Among various amino acids constituting peptides, glycine is the basic skeleton of amino acids and plays crucial roles in nutrition, metabolism, and the synthesis of a variety of biomolecules, such as purine nucleotides and creatine . It accounts for 11.5% of total amino acids and 20% of amino acid nitrogen in body proteins .…”

“…1 Among various amino acids constituting peptides, glycine is the basic skeleton of amino acids and plays crucial roles in nutrition, metabolism, and the synthesis of a variety of biomolecules, such as purine nucleotides and creatine. 2 It accounts for 11.5% of total amino acids and 20% of amino acid nitrogen in body proteins. 3 Despite the fact that natural amino acids and peptides continue to be of great significance, the transformation of glycine into nonproteinogenic amino acids and modification of glycine-containing peptides may remarkably improve their activities, pharmacological properties, and pharmacokinetics as compared to their natural counterparts.…”