TY - JOUR
T1 - Total 1H NMR assignment of 3β-acetoxypregna-5,16-dien-20-one
AU - Becerra-Martinez, Elvia
AU - Ramírez-Gualito, Karla E.
AU - Pérez-Hernández, Nury
AU - Joseph-Nathan, Pedro
N1 - Publisher Copyright:
© 2015 Elsevier Inc. All rights reserved.
PY - 2015/12/1
Y1 - 2015/12/1
N2 - This work describes the total and unambiguous assignment of the 750 MHz 1H NMR spectrum of 3β-acetoxypregna-5,16-dien-20-one or 16-DPA (1), the well-known intermediate utilized in the synthesis of biological important commercial steroids. The task was accomplished by extracting the coupling constant values in the overlapped spectrum region by HSQC, and using these values in the 1H iterative full spin analysis integrated in the PERCH NMR software. Comparison of the experimental vicinal coupling constants of 1 with the values calculated using Altona provides an excellent correlation. The same procedure, when applied to the published data of progesterone (2) and testosterone (3), afforded an acceptable correlation for 2 and a poor correlation for 3. In the last case, this suggested the reassignment of all four vicinal coupling constants for the methylene signals at the C-15 and C-16 positions, demonstrating the utility of this methodology.
AB - This work describes the total and unambiguous assignment of the 750 MHz 1H NMR spectrum of 3β-acetoxypregna-5,16-dien-20-one or 16-DPA (1), the well-known intermediate utilized in the synthesis of biological important commercial steroids. The task was accomplished by extracting the coupling constant values in the overlapped spectrum region by HSQC, and using these values in the 1H iterative full spin analysis integrated in the PERCH NMR software. Comparison of the experimental vicinal coupling constants of 1 with the values calculated using Altona provides an excellent correlation. The same procedure, when applied to the published data of progesterone (2) and testosterone (3), afforded an acceptable correlation for 2 and a poor correlation for 3. In the last case, this suggested the reassignment of all four vicinal coupling constants for the methylene signals at the C-15 and C-16 positions, demonstrating the utility of this methodology.
KW - 3β-Acetoxypregna-5,16-dien-20-one
KW - Iterative H NMR analysis
KW - Progesterone
KW - Testosterone
UR - http://www.scopus.com/inward/record.url?scp=84947943827&partnerID=8YFLogxK
U2 - 10.1016/j.steroids.2015.10.005
DO - 10.1016/j.steroids.2015.10.005
M3 - Artículo
SN - 0039-128X
VL - 104
SP - 208
EP - 213
JO - Steroids
JF - Steroids
ER -