GC/MS * 20 DNA. Alves and Payne, 1980; Payne and Smith, 1994; Smith et al., 1999 Pseudoalteromonas sp. 10,000. Zhang et al., 2010.

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1 Res. Org. Geochem. 27, (2011) 30 No.24 GC/MS * ** DNA 10,000 N- 2 2 Steinberg and Bada, 1983; Sepetov et al., 1991 Alves and Payne, 1980; Payne and Smith, 1994; Smith et al., 1999 Pseudoalteromonas sp. Zhang et al., 2010 glycylglycine Gly-GlyShimoyama and Ogasawara, /400 * Dipeptides in Tokyo Bay sediment Analyses of dipeptides by GC/MS ** Hajime Mita, Department of Life, Environment and Materials, Science Faculty of Engineering, Fukuoka Institute of Technology , Wajiro-Higashi, Higashi-Ku, Fukuoka, FUKUOKA , Japan 143

2 HPLC HPLC HPLC GC/MSGC GC 3 Ogasawara et al., S cm 2 g 3 ml 60 1 h ml 3 mol/l HCl ph 1.8 Dowex 50W-X8H + 10 cm 1 cmid25 ml 25 ml 1.2 mol/l ph HPLC Spackman et al., ml 1.5 mol/l HCl- 3 h 1 ml 30 min 50 μl 1 μl GC-MS Shimadzu, GC-MS QP-5000 GC Chirasil-L-Val Chrompcak Internationa Inc., 25 m 0.25 mmid 1 ml/min /min /min 20 min /min /min 200 ev 1 s m/z s 34 Fig GC/MS Selective ion chromatogram, SICFig Table 1 Fig Fig. 3glycyl-L- 144

3 GC/MS Fig. 1. Schematic diagram of dipeptide analysis in sedimentary rock. Fig. 2. Selective ion chromatograms of N-trifluoroacetyl methyl esters of dipeptides in water extract of the sample at 1.3 cm in depth of the sediment core S8602 of Tokyo Bay. The m/z ions correspond to (M+1) +, where M stands for a molecular weight of each dipeptide derivative. Peak numbers (1-34) correspond to those of compounds in Table 1. (Ogasawara et al., 2001) Table 1. Concentrations of dipeptides in water extracts of the sample at surface ofthe sediment core S8602 of Tokyo Bay No. Compound name Configuration m/z * Retention Concentration time/min ** / nmol g -1 1 glycylglycine glycylalanine L alanylglycine L a alanylalanine DD b alanylalanine DL c alanylalanine LD d alanylalanine LL glycylvaline L valylglycine L glycylleucine L leucylglycine L glycylisoleucine L alanylvaline LL valylalanine LL alanylleucine LL leucylalanine LL alanylisoleucine LL glycylaspartic acid L aspartylglycine L valylvaline LL alanylaspartic acid LL aspartylalanine LL glycylphenylalanine L phenylalanylglycine L valylleucine LL leucylvaline LL glutamylalanine LL alanylphenylalanine LL phenylalanylalanine LL leucylleucine LL valylaspartic acid LL aspartylvaline LL valylglutamic acid LL leucylaspartic acid LL valylphenylalanine LL leucylphenylalanine LL phenylalanylleucine LL Total 80 * Mass numbers used for identifi cation of dipeptides on massfragmentograms. ** All compounds were identifi ed by coincidence in mass spectra and retention times with those of authentic compounds. valine Gly-L-Val L-valylglycine L-Val-Gly Fig. 3c, d 5 N- C- alanylvaline Ala-Val 145

4 valylalanine Val-Ala Ala-Val alanylleucine Ala-Lue luecylalanine Lue-Ala Lue-Ala N- C- 34 Fig. 3. Mass spectra of N-trifluoroacetyl methyl esters of a) L-ala-L-ala, b) gly-gly, c) L-val-gly, and d) gly- L-val standards obtained bynthe chemical ionization mode. (Ogasawara et al., 2000) Islam and Darbre, 1972; Knapp, h < % Ogasawara et al., h L- L-Val-Gly L- < 0.2% L-alanyl-L-alanine L-Ala-L-Ala D-Ala-D-Ala D-Ala-L-AlaL-Ala-D-Ala 2 4 Fig. 4 Ala-Ala 4 L-Ala-L-Ala D-Ala-D-Ala D-Ala-L-AlaL-Ala-D-Ala L- Ala-L-Ala D-Ala-L-Ala L-Ala-D-Ala D-Ala-D-Ala D-Ala-D-Ala D-Ala-L-Ala L-Ala-D- Ala D-Ala L-Ala-L-Ala Gly-Val Gly-L-Val Gly-D-Val Ogasawara et al., 2000 glycyl-l-aspartic acid Gly-L-AspL-Ala-L-Ala Gly-D-Asp D-Ala-L-alaL-Ala-D-AlaD-Ala-D-ala < 0.1% 146

5 GC/MS Fig. 4. Selective ion chromatograms of N-trifluoroacetyl methyl esters of ala-ala diastereomers (m/z 271) and gly-val diasteromers (m/z 285) in water extract of the sample at 1.3 cm in depth of the sediment core S8602 of Tokyo Bay. (Ogasawara et al., 2000) nmol/g nmol/g nmol/g Ogasawara et al., 2001Gly nmol/g Gly 2.7% Gly Ogasawara et al., 2000 Hill, 1965 N- 2 Steinberg and Bada, 1983; Sepetov et al., 1991 Smith and Baum, 1987; Steinberg and Bada, 1983 Ogasawara et al., 2001 C- D-ala-D-ala Ogasawara et al., 2000 Zhang et al., H20 Alves R.A. and Payne J.W. (1980) The number and nature of the peptide transport systems of E. coli: characterization of specific transport mutants. Biochem. Soc. Trans. 8, Hill R.L. (1965) Hydrolysis of proteins. Adv. Protein 147

6 Chem. 20, Islam A. and Darbre A. (1972) Gas-liquid chromatography of trifluoroacetyleted amino acid methyl esters. Determination of their molar responses with flame ioniation detector. J. Chromatogr. 71, Knapp D.R. (1979) Handbook of analytical derivatization reactions. John Wiley & Sons (NewYork). Ogasawara R., Ishiwatari R. and Shimoyama A. (2001) Detection of water extractable dipeptides and their characteristics in recent sediments of Tokyo Bay. Geochem. J. 35, Ogasawara R., Mita H., Ishiwatari R. and Shimoyama A. (2000) Analysis of water-extractable dipeptides from sediments by gas chromatography-mass spectrometry. Res. Org. Geochem. 15, Payne J.W. and Smith M.W. (1994) Peptide transport by microorganisms. Adv. Microb. Physiol. 36, Sepetov M.F., Krymsky M.A., Ovchinnikov M.V., Bespaloba Z.D., Isakova O.L., Soueck M. and Lebi M. (1991) Rearrangement, racemizition and decomposition of peptides in aqueous solution. Peptide Res. 4, Shimoyama A. and Ogasawara R. (2002) Dipetides and diketopiperazines in the Yamato and Murchison carbonaceous chondrites. Origin Life Evol. Biosphere 32, Smith G.G. and Baum R. (1987) First-order rate constants for the racemization of each component in a mixture of isomeric dipeptides and their diketopiperazines. J. Org. Chem. 52, Smith M.W., Tyreman D.R., Payne G.M., Marshall N.J. and Payne J.W. (1999) Substrate specificity of the periplasmic dipeptide-binding protein from Escherichia coli: experimental basis for the design of peptide prodrugs. Microbiol. 145, Spackman D.H., Stein W.H. and Moore S. (1958) Automatic recording apparatus for use in the chromatography of amino acids. Anal. Chem. 30, Steinberg S.M. and Bada J.L. (1983) Peptide decomposition in the neutral ph region via the formation of diketopiperazines. J. Org. Geochem. 48, Zhang W.-X., Xie B.-B., Chen X.-L., Dong S., Zhang X.-Y., Zhou B.-C. and Zhang Y.-Z. (2010) Domains III and I-2a, at the Entrance of the Binding Cleft, Play an Important Role in Cold Adaptation of the Periplasmic Dipeptide-Binding Protein (DppA) from the Deep-Sea Psychrophilic Bacterium Pseudoalteromonas sp. Strain SM9913. Appl. Environ. Microbiol. 76,

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