Ab Initio and DFT Computational Study …
211
Table 1 Symbols utilised to denote the main geometry features in the acronyms denoting the
conformers of myristinin A, cis-DBPO and trans-DBPO. The meaning of the symbols is also
illustrated in Fig. 4
Symbol Geometrical feature
d
The first IHB is on the same side as R (H15···O14)
s
The first IHB is on the other side with respect to R (H17···O14)
r
The C3–C4–O10–H16 torsion angle is close to 0 o
w
The C3–C4–O10–H16 torsion angle is close to 180 o
u
The OH ortho to CRO and not engaged in the first IHB is oriented toward the acyl
group
non-u
The OH ortho to CRO and not engaged in the first IHB is oriented away from the
acyl group
η
Presence of O–H···π interaction between H16 and ring B
ε
Presence of O–H···π interaction between H15 and ring B
a
C19 in ring D is above the plane identified by C9, C23, C22 and O21
b
C19 in ring D is below the plane identified by C9, C23, C22 and O21
p
The B,D ring system is oriented ‘towards us’ and ring E ‘towards the back’ with
reference to Fig. 2
q
The B,D ring system is oriented ‘towards the back’ and ring E ‘towards us’ with
reference to Fig. 2
e
O28–H29 is oriented to the side of C27
f
O28–H29 is oriented to the side of the phloroglucinol moiety
j
O36–H37 is oriented to the side of C34
k
O36–H37 is oriented to the side of the phloroglucinol moiety
y
At the input level, the bond specified by the number preceding the y has been rotated
by -90° with respect to the linear geometry of R shown in Fig. 3
z
at the input level, the bond specified by the number preceding the z has been rotated
by +90° with respect to the linear geometry of R shown in Fig. 3
v
At the input level, the bond specified by the number preceding the v has been rotated
by 180° (toward the other side with respect to R ) with respect to the linear geometry
of R shown in Fig. 3
x
At the input level, the bond specified by the number preceding the x has been rotated
by 180° (toward the side of R ) with respect to the linear geometry of R shown in
Fig. 3
1–10
Numbers denoting the single bonds of R, as shown in Fig. 3
side as R
(d), the C3–C4–O10–H16 torsion angle is close to 0° (r), the O10–H16···π
IHB with ring B is present (η), the B,D ring system is oriented ‘towards us’ and ring
E ‘towards the back’ with reference to Fig. 2 (p), C19 in ring D is above the plane
identified by C9, C23, C22 and O21 (a), O28–H29 is oriented to the side of C27 (e),
O36–H37 is oriented to the side of C34 (j), and the R chain is on the same plane as
ring A (absence of no specifications about bond rotations); MYRA-d-r-η-p-a-e-j-2y
is a conformer of MYRA with the same other features as MYRA-d-r-η-p-a-e-j, but
211
Table 1 Symbols utilised to denote the main geometry features in the acronyms denoting the
conformers of myristinin A, cis-DBPO and trans-DBPO. The meaning of the symbols is also
illustrated in Fig. 4
Symbol Geometrical feature
d
The first IHB is on the same side as R (H15···O14)
s
The first IHB is on the other side with respect to R (H17···O14)
r
The C3–C4–O10–H16 torsion angle is close to 0 o
w
The C3–C4–O10–H16 torsion angle is close to 180 o
u
The OH ortho to CRO and not engaged in the first IHB is oriented toward the acyl
group
non-u
The OH ortho to CRO and not engaged in the first IHB is oriented away from the
acyl group
η
Presence of O–H···π interaction between H16 and ring B
ε
Presence of O–H···π interaction between H15 and ring B
a
C19 in ring D is above the plane identified by C9, C23, C22 and O21
b
C19 in ring D is below the plane identified by C9, C23, C22 and O21
p
The B,D ring system is oriented ‘towards us’ and ring E ‘towards the back’ with
reference to Fig. 2
q
The B,D ring system is oriented ‘towards the back’ and ring E ‘towards us’ with
reference to Fig. 2
e
O28–H29 is oriented to the side of C27
f
O28–H29 is oriented to the side of the phloroglucinol moiety
j
O36–H37 is oriented to the side of C34
k
O36–H37 is oriented to the side of the phloroglucinol moiety
y
At the input level, the bond specified by the number preceding the y has been rotated
by -90° with respect to the linear geometry of R shown in Fig. 3
z
at the input level, the bond specified by the number preceding the z has been rotated
by +90° with respect to the linear geometry of R shown in Fig. 3
v
At the input level, the bond specified by the number preceding the v has been rotated
by 180° (toward the other side with respect to R ) with respect to the linear geometry
of R shown in Fig. 3
x
At the input level, the bond specified by the number preceding the x has been rotated
by 180° (toward the side of R ) with respect to the linear geometry of R shown in
Fig. 3
1–10
Numbers denoting the single bonds of R, as shown in Fig. 3
side as R
(d), the C3–C4–O10–H16 torsion angle is close to 0° (r), the O10–H16···π
IHB with ring B is present (η), the B,D ring system is oriented ‘towards us’ and ring
E ‘towards the back’ with reference to Fig. 2 (p), C19 in ring D is above the plane
identified by C9, C23, C22 and O21 (a), O28–H29 is oriented to the side of C27 (e),
O36–H37 is oriented to the side of C34 (j), and the R chain is on the same plane as
ring A (absence of no specifications about bond rotations); MYRA-d-r-η-p-a-e-j-2y
is a conformer of MYRA with the same other features as MYRA-d-r-η-p-a-e-j, but