stable 2 Proton-NMR spectra of the MGP esters 20 3 four 5 6 7 8 9 ten five.63 (1H, d, J 8.0)Compounds (chemical shifts, ppm, Hz)ProtonsH-H-6aH-6bGlycoconjugate Journal (2022) 39:261H-4.40 (1H, dd, J 11.1 and 6.six) 4.20 (1H, dd, J 11.two and 6.8) four.65 (1H, d, J three.7)H-H-4.96 (1H, d, J eight.0) 4.85 (1H, dd, J 11.1 and 6.5) four.72 (1H, dd, J 11.1 and 6.7) 4.22 (1H, d, J three.5) 4.09 (1H, dd, J three.0 and ten.five) three.88 (1H, dd, J eight.0 and ten.5) 3.58 (1H, m) 3.36 (3H, s) 2.38 (2H, m) 1.64 (2H, m) 1.25 (20H, m) 0.96 (3H, m) 2.21, 2.14, two.11 (three 3H, three s) two.36 (6H, m) 1.68 (6H, m) 0.98 (3H, m) 2.31 (6H, m) 1.24 (78H, m) 0.91 (9H, m) 0.96 (3H, m) 0.94 (3H, m) 0.93 (3H, m) 1.28 (20H, m) 1.26 (20H, m) 1.32 (20H, m) 1.24 (20H, m) 0.91 (3H, m) 1.25 (20H, m) 0.88 (3H, m) 1.27 (20H, m) 0.98 (3H, m)4.94 (1H, d, J 8.0) four.11 (1H, dd, J 11.two and six.six) three.94 (1H, dd, J 11.two and six.8) 4.68 (1H, d, J three.five) 4.74 (1H, dd, J three.3 and 10.7) four.81 (1H, dd, J 8.0 and ten.4) three.88 (1H, m) 3.45 (3H, s) two.36 (2H, m) 1.68 (2H, m)five.41 (1H, d, J eight.two) four.22 (1H, dd, J 11.1 and 6.eight) 4.16 (1H, dd, J 11.0 and 6.8) 4.46 (1H, d, J three.five 5.13 (1H, dd, J 3.2 and ten.six) 5.21 (1H, dd, J 8.1 and ten.5) 3.92 (1H, m) 3.45 (3H, s) 2.35 (2H, m) 1.66 (2H, m)five.38 (1H, d, J 8.3) four.39 (1H, dd, J 11.2 and six.7) four.14 (1H, dd, J 11.0 and six.7) 4.75 (1H, d, J three.six) five.03 (1H, dd, J 3.1 and 10.six) 5.16 (1H, dd, J eight.0 and ten.5) three.99 (1H, m) three.47 (3H, s) 2.34 (2H, m) 1.64 (2H, m)five.30 (1H, d, J eight.1) 4.40 (1H, dd, J 11.2 and six.6) four.11 (1H, dd, J 11.two and 6.8) 4.85 (1H, d, J 3.7) 5.01 (1H, dd, J 3.2 and ten.6) five.15 (1H, dd, J 8.two and 10.six) 3.51 (1H, m) 3.45 (3H, s) 2.31 (2H, m) 1.62 (2H, m)5.22 (1H, d, J 8.0) four.30 (1H, dd, J 11.1 and six.6) 4.10 (1H, dd, J 11.0 and six.7) four.55 (1H, d, J three.6) 4.75 (1H, dd, J 3.0 and 10.six) five.05 (1H, dd, J eight.1 and 10.6) 3.91 (1H,m) 3.56 (3H, s) 2.32 (2H, m) 1.61 (2H, m)five.48 (1H, d, J eight.2) 4.40 (1H, dd, J 11.two and six.6) 4.01 (1H, dd, J 11.2 and six.8) four.66 (1H, d, J three.7) five.05 (1H, dd, J 3.two and 10.6) five.34 (1H, dd, J 8.2 and 10.6) three.52 (1H, m) three.50 (3H, s) 2.33 (2H, m) 1.63 (2H, m)five.23 (1H, d, J eight.1) 4.27 (1H, dd, J 11.0 and six.5) four.11 (1H, dd, J 11.1 and 6.9) 4.53 (1H, d, J 3.5) four.77 (1H, dd, J 3.1 and 10.five) 5.08 (1H, dd, J eight.0 and ten.five) three.98 (1H, m) 3.46 (3H, s) 2.37 (2H, m) 1.63 (2H, m)five.01 (1H, dd, J three.0 and ten.5) five.21 (1H, dd, J 8.two and 10.six) four.00 (1H, m) 3.46 (3H, s) two.35 (2H, m) 1.65 (2H, m) 1.24 (20H, m) 0.86 (3H, m)1.28 (20H, m)H-5 1-OCH3 CH3(CH2)11CH2CO CH3(CH2)10CH2CH 2CO CH3(CH2)10CH2CH 2CO CH3(CH2)12CO 3 CH3CO0.94 (3H, m)3 CH3CH2CH2CO 3 CH3CH2CH2CO 3 CH3(CH2)2CO 3 CH3(CH2)13CH2CO 3 CH3(CH2)13CH2CO 3 CH3(CH2)14CO 3 CH3(CH2)15CH2CO three CH3(CH2)15CH2CO 3 CH3(CH2)1 three Ar2.27 (6H, m) 1.29 (90H, m) 0.90 (9H, m)3 PhCH = CHCO7.67 (18H, m) 7.45 (27H, m)7.54 (6H, m) 7.28 (9H, m) 7.75 7.52, 7.37 (3 1H, 3 d, J 16.8.03 (6H, m) 7.94 (6H, m)Glycoconjugate Journal (2022) 39:261and are presented in Table four, Figs. 6, 7. The compounds CCR9 review showed promising inhibitory activity against many each Gram-positive and Gram-negative bacteria. The inhibition information (Table 4) indicated that compound four showed the highest activity (39 0.4 mm); compounds 2 (29 0.four mm), three (21 0.3 mm), 8 (25 0.3 mm), and ten (34 0.4 mm) have been also exhibited an excellent inhibition activity against Bacillus subtilis than the normal antibiotic JNK1 Accession azithromycin (19 0.3 mm). However, compound 10 (26 0.3 mm) showed additional activity than normal drug on Staphylococcus aureus. Nonetheless, compounds 3 (20 0.three mm), four (22 0.3 mm), 6 (20 0.three mm), 7 (18 0.3 mm), and ten (3