Compounds, methods, complexes, apparatuses and uses relating to stabile forms of NAD/NADH

1. A coenzyme for a dehydrogenase, comprising a compound of the following general formula (I″) or a salt thereof or a form thereof having a reduced nicotinamide ring:

in which:

A=adenine or an analog thereof selected from the group consisting of C 8 -substituted adenine, N 6 -substituted adenine, 7-deaza-adenine, 8-aza-adenine, 7-deaza-8-aza-adenine and formycin,

T=O or S,

U=OH, SH, BH 3 − , or BCNH 2 − ,

V=OH or a phosphate group,

W=COOR, CON(R) 2 , COR, or CSN(R) 2 , in which R=H or C 1 -C 2 alkyl,

X 1 , X 2 =O, CH 2 , NH, or NCH 3 ,

Y=NH, S, O, or CH 2 , and

Z=a saturated or unsaturated carbocyclic or heterocyclic six-membered ring, and a residue C(R 4 ) 2 bound to the six-membered ring and to X 2 , where R 4 =H, F, Cl, or CH 3 , wherein the six-membered ring and the pyridine residue are not linked by a glycosidic bond.

2. The coenzyme of claim 1 , wherein Z comprises a compound of the general formula (II):

in which a single or double bond can in each case independently be present between R 1 and R 2 or between R 1 ′ and R 2 ′, wherein if a single bond is present between R 1 and R 2 or R 1 ′ and R 2 ′ respectively:

R 1 , R 1 ′=O, S, NCH 3 , NH, C(R 4 ) 2 , CHOH, or CHOCH 3 , where R 1 or R 1 ′ cannot at the same time be a heteroatom, and

R 2 , R 2 ′=C(R 4 ) 2 , CHOH, CHOCH 3 ;

and wherein if a double bond is present between R 1 and R 2 or R 1 ′ and R 2 ′ respectively:

R 1 , R 1 ′, R 2 , R 2 ′=CR 4 , and

R 4 =H, F, Cl, or CH 3 ;

and in which R 6 , R 6 ′=CH or CCH 3 .

3. The coenzyme of claim 1 , wherein W=CONH 2 or COCH 3 .

4. The coenzyme of claim 1 having the following general formula (III) or a salt thereof or a form thereof having a reduced nicotinamide ring:

in which:

U=OH, SH, BH 3 − , or BCNH 2 − ,

V=OH or a phosphate group,

W=COOR, CON(R) 2 , COR, CSN(R) 2 where R=H or C 1 -C 2 alkyl,

X=O, CH 2 , or NH,

R 1 =C(R 4 ) 2 , O, S, NCH 3 , NH, CH, CHOH, CHOH 3 , wherein R 4 =H, F, Cl, CH 3 , and

R 4 ′=H or OH.

5. The coenzyme of claim 4 having the following general formula (IV) or a salt thereof or a form thereof having a reduced nicotinamide ring:

in which:

X=O, CH 2 , NH, or NCH 3 .

6. The coenzyme of claim 4 having the following general formula (V) or a salt thereof or a form thereof having a reduced nicotinamide ring:

in which:

X=O, CH 2 , NH, or NCH 3 .

7. The coenzyme of claim 4 having the following general formula (VI) or a salt thereof or a form thereof having a reduced nicotinamide ring:

in which:

X=O, CH 2 , NH, or NCH 3 .

8. An enzyme-coenzyme complex comprising the coenzyme of claim 1 in combination with a suitable dehydrogenase.

9. An enzyme-coenzyme complex comprising the coenzyme of claim 4 in combination with a suitable dehydrogenase.

10. The complex of claim 8 , which comprises a dehydrogenase selected from the group consisting of glucose dehydrogenase, lactate dehydrogenase, malate dehydrogenase, glycerol dehydrogenase, alcohol dehydrogenase, alpha-hydroxybutyrate dehydrogenase, sorbitol dehydrogenase, and amino acid dehydrogenase selected from an L-amino acid dehydrogenase.

11. A reagent matrix comprising the complex of claim 8 in combination with a suitable reaction buffer.

12. The reagent matrix of claim 11 , which comprises a dehydrogenase selected from the group consisting of a glucose dehydrogenase, lactate dehydrogenase, malate dehydrogenase, glycerol dehydrogenase, alcohol dehydrogenase, alpha-hydroxybutyrate dehydrogenase, sorbitol dehydrogenase, and amino acid dehydrogenase such as a L-amino acid dehydrogenase.

13. A method for detecting an analyte comprising the steps of:

(a) contacting a sample with the reagent matrix of claim 11 , and

(b) detecting the analyte by one of electrochemistry, photometry or fluorometry.

14. A compound of the following general formula (I″) or a salt thereof:

in which:

A=adenine or an analog thereof selected from the group consisting of C 8 -substituted adenine, N 6 -substituted adenine, 7-deaza-adenine, 8-aza-adenine, 7-deaza-8-aza-adenine and formycin,

T=O or S,

U=OH, SH, BH 3 − , or BCNH 2 − ,

V=OH or a phosphate group,

W=COOR, CON(R) 2 , COR, or CSN(R) 2 , in which R=H or C 1 -C 2 alkyl,

X 1 , X 2 =O, CH 2 , NH, or NCH 3 ,

Y=NH, S, O, or CH 2 , and

Z=a saturated or unsaturated carbocyclic or heterocyclic six-membered ring, and a residue C(R 4 ) 2 bound to the six-membered ring and to X 2 , where R 4 =H, F, Cl, or CH 3 , wherein the six-membered ring and the pyridine residue are not linked by a glycosidic bond.

15. The coenzyme of claim 1 , wherein the 7-deaza-adenine or 7-deaza-8-aza-adenine is substituted in the 7 position with a member selected from the group consisting of a halogen, a C 1 -C 6 alkinyl, a C 1 -C 6 alkenyl, and a C 1 -C 6 alkyl.

16. The coenzyme of claim 14 , wherein the 7-deaza-adenine or 7-deaza-8-aza-adenine is substituted in the 7 position with a member selected from the group consisting of a halogen, a C 1 -C 6 alkinyl, a C 1 -C 6 alkenyl, and a C 1 -C 6 alkyl.