SPDS eBook March 2017

Challenge: SAMe’s Extreme Instability

NH 2

(1) Racemization

N

N

CH 3

(S)

_

+

(S)

S

OOC H 2 N

N N

Positive Points about (R, S) SAMe: • It is still SAMe; • It is not harmful; • It is reversible to Bioactive (S, S) SAMe;

O

(S, S) SAMe

H

Bio-Active Form

HO OH

Reversible Conversion

NH 2

N

N

It is possible that (R, S) is a Time Release form of (S, S).

•

(R)

_

+

(S)

OOC H 2 N

S

N N

O

(R, S) SAMe Bio-Inactive Form

CH 3

H

HO OH

Challenge: SAMe’s Extreme Instability

(2) Degradation

S -Adenosyl-L- Homocysteine (SAH)

Adenosine (ADE)

SAMe

• • • • • • Loss is – permanent, Irreversible and Significant

5’-Deoxy-5’- Methylthioadenosine (DMTA)